|
|
char = T;code = 84
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char = :;code = 58
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char = c;code = 99
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char = ;code = 32
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char = o;code = 111
char = l;code = 108
char = ;code = 32
char = o;code = 111
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char = e;code = 101
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result sql = Taming the Chlorine Radical: Enforcing Steric Control over Chlorine-Radical-Mediated C-H Activation.
Taming the Chlorine Radical: Enforcing Steric Control over Chlorine-Radical-Mediated C-H Activation.char = C;code = 67
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char = l;code = 108
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char = a;code = 97
char = l;code = 108
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char = r;code = 114
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char = a;code = 97
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char = l;code = 108
char = y;code = 121
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char = c;code = 99
char = t;code = 116
char = i;code = 105
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char = a;code = 97
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char = e;code = 101
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char = C;code = 67
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char = H;code = 72
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char = u;code = 117
char = t;code = 116
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char = t;code = 116
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char = e;code = 101
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char = i;code = 105
char = g;code = 103
char = h;code = 104
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char = z;code = 122
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char = a;code = 97
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char = W;code = 87
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char = t;code = 116
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char = c;code = 99
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char = i;code = 105
char = v;code = 118
char = i;code = 105
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char = S;code = 83
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char = I;code = 73
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char = a;code = 97
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char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = i;code = 105
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = s;code = 115
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = C;code = 67
char = l;code = 108
char = ·;code = 183
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = v;code = 118
char = i;code = 105
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = m;code = 109
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = f;code = 102
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = o;code = 111
char = r;code = 114
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = .;code = 46
char = <;code = 60
char = b;code = 98
char = r;code = 114
char = >;code = 62
char = <;code = 60
char = b;code = 98
char = r;code = 114
char = >;code = 62
result sql = Chlorine radicals readily activate C-H bonds, but the high reactivity of these intermediates precludes their use in regioselective C-H functionalization reactions. We demonstrate that the secondary coordination sphere of a metal complex can confine photoeliminated chlorine radicals and afford steric control over their reactivity. Specifically, a series of iron(III) chloride pyridinediimine complexes exhibit activity for photochemical C(sp3)-H chlorination and bromination with selectivity for primary and secondary C-H bonds, overriding thermodynamic preference for weaker tertiary C-H bonds. Transient absorption spectroscopy reveals that Cl· remains confined through formation of a Cl·|arene complex with aromatic groups on the pyridinediimine ligand. Furthermore, photocrystallography confirms that this selectivity arises from the generation of Cl· within the steric environment defined by the iron secondary coordination sphere.
char = a;code = 97
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = C;code = 67
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = R;code = 82
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = :;code = 58
char = ;code = 32
char = E;code = 69
char = n;code = 110
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = c;code = 99
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = S;code = 83
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = C;code = 67
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = o;code = 111
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = C;code = 67
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = -;code = 45
char = R;code = 82
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = -;code = 45
char = M;code = 77
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = C;code = 67
char = -;code = 45
char = H;code = 72
char = ;code = 32
char = A;code = 65
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = .;code = 46
result sql = Taming the Chlorine Radical: Enforcing Steric Control over Chlorine-Radical-Mediated C-H Activation.
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = C;code = 67
char = -;code = 45
char = H;code = 72
char = ;code = 32
char = b;code = 98
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = b;code = 98
char = u;code = 117
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = e;code = 101
char = c;code = 99
char = l;code = 108
char = u;code = 117
char = d;code = 100
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = g;code = 103
char = i;code = 105
char = o;code = 111
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = C;code = 67
char = -;code = 45
char = H;code = 72
char = ;code = 32
char = f;code = 102
char = u;code = 117
char = n;code = 110
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = z;code = 122
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = W;code = 87
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = m;code = 109
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = t;code = 116
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = o;code = 111
char = r;code = 114
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = x;code = 120
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = n;code = 110
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = f;code = 102
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = e;code = 101
char = l;code = 108
char = i;code = 105
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = a;code = 97
char = f;code = 102
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = d;code = 100
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = o;code = 111
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = .;code = 46
char = ;code = 32
char = S;code = 83
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = i;code = 105
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = i;code = 105
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = (;code = 40
char = I;code = 73
char = I;code = 73
char = I;code = 73
char = );code = 41
char = ;code = 32
char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = y;code = 121
char = r;code = 114
char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = d;code = 100
char = i;code = 105
char = i;code = 105
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = l;code = 108
char = e;code = 101
char = x;code = 120
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = h;code = 104
char = i;code = 105
char = b;code = 98
char = i;code = 105
char = t;code = 116
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = p;code = 112
char = h;code = 104
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = c;code = 99
char = h;code = 104
char = e;code = 101
char = m;code = 109
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = C;code = 67
char = (;code = 40
char = s;code = 115
char = p;code = 112
char = <;code = 60
char = s;code = 115
char = u;code = 117
char = p;code = 112
char = >;code = 62
char = 3;code = 51
char = <;code = 60
char = /;code = 47
char = s;code = 115
char = u;code = 117
char = p;code = 112
char = >;code = 62
char = );code = 41
char = -;code = 45
char = H;code = 72
char = ;code = 32
char = c;code = 99
char = h;code = 104
char = l;code = 108
char = o;code = 111
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = l;code = 108
char = e;code = 101
char = c;code = 99
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char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = i;code = 105
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char = a;code = 97
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char = y;code = 121
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char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = s;code = 115
char = e;code = 101
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = C;code = 67
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char = H;code = 72
char = ;code = 32
char = b;code = 98
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char = d;code = 100
char = s;code = 115
char = ,;code = 44
char = ;code = 32
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char = e;code = 101
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char = i;code = 105
char = d;code = 100
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = r;code = 114
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char = d;code = 100
char = y;code = 121
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char = a;code = 97
char = m;code = 109
char = i;code = 105
char = c;code = 99
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char = c;code = 99
char = e;code = 101
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = a;code = 97
char = k;code = 107
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = t;code = 116
char = i;code = 105
char = a;code = 97
char = r;code = 114
char = y;code = 121
char = ;code = 32
char = C;code = 67
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char = H;code = 72
char = ;code = 32
char = b;code = 98
char = o;code = 111
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char = d;code = 100
char = s;code = 115
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char = ;code = 32
char = T;code = 84
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char = a;code = 97
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char = s;code = 115
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char = e;code = 101
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char = t;code = 116
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char = b;code = 98
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char = i;code = 105
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char = c;code = 99
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char = y;code = 121
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char = e;code = 101
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char = e;code = 101
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
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char = C;code = 67
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char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = g;code = 103
char = r;code = 114
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char = ;code = 32
char = o;code = 111
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char = ;code = 32
char = t;code = 116
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char = d;code = 100
char = i;code = 105
char = i;code = 105
char = m;code = 109
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char = l;code = 108
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char = l;code = 108
char = o;code = 111
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char = r;code = 114
char = a;code = 97
char = p;code = 112
char = h;code = 104
char = y;code = 121
char = ;code = 32
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char = i;code = 105
char = r;code = 114
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char = s;code = 115
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char = t;code = 116
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char = t;code = 116
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char = e;code = 101
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char = s;code = 115
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char = ;code = 32
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char = t;code = 116
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char = n;code = 110
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char = ;code = 32
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char = i;code = 105
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char = ;code = 32
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char = ;code = 32
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char = t;code = 116
char = e;code = 101
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char = ;code = 32
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char = o;code = 111
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char = ;code = 32
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char = ;code = 32
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char = o;code = 111
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char = d;code = 100
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char = n;code = 110
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = .;code = 46
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result sql = Chlorine radicals readily activate C-H bonds, but the high reactivity of these intermediates precludes their use in regioselective C-H functionalization reactions. We demonstrate that the secondary coordination sphere of a metal complex can confine photoeliminated chlorine radicals and afford steric control over their reactivity. Specifically, a series of iron(III) chloride pyridinediimine complexes exhibit activity for photochemical C(sp3)-H chlorination and bromination with selectivity for primary and secondary C-H bonds, overriding thermodynamic preference for weaker tertiary C-H bonds. Transient absorption spectroscopy reveals that Cl· remains confined through formation of a Cl·|arene complex with aromatic groups on the pyridinediimine ligand. Furthermore, photocrystallography confirms that this selectivity arises from the generation of Cl· within the steric environment defined by the iron secondary coordination sphere.
Publication: J Am Chem Soc 2022 Jan
Publication Date: Jan 2022
Study Author(s): Gonzalez Miguel I MI ; Gygi David D ; Qin Yangzhong Y ; Zhu Qilei Q ; Johnson Elizabeth J EJ ; Chen Yu-Sheng YS ; Nocera Daniel G DG ;
Institution: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
Shortcut link to this study:
Publication Date: Jan 2022
Study Author(s): Gonzalez Miguel I MI ; Gygi David D ; Qin Yangzhong Y ; Zhu Qilei Q ; Johnson Elizabeth J EJ ; Chen Yu-Sheng YS ; Nocera Daniel G DG ;
Institution: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
Shortcut link to this study:
Chlorine radicals readily activate C-H bonds, but the high reactivity of these intermediates precludes their use in regioselective C-H functionalization reactions. We demonstrate that the secondary coordination sphere of a metal complex can confine photoeliminated chlorine radicals and afford steric control over their reactivity. Specifically, a series of iron(III) chloride pyridinediimine complexes exhibit activity for photochemical C(sp3)-H chlorination and bromination with selectivity for primary and secondary C-H bonds, overriding thermodynamic preference for weaker tertiary C-H bonds. Transient absorption spectroscopy reveals that Cl· remains confined through formation of a Cl·|arene complex with aromatic groups on the pyridinediimine ligand. Furthermore, photocrystallography confirms that this selectivity arises from the generation of Cl· within the steric environment defined by the iron secondary coordination sphere.
PMID: 35020391
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