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84935012914
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note
-
The treatment of 3a with sodium hydride gave the N?O bond cleavage product in 85% yield. For details, see the SI.
-
-
-
-
53
-
-
84934932673
-
-
note
-
We studied the effect of the nitrogen substituents by DFT calculations. The change of the OMe group to Ph and Me groups increases the C-H amination barrier from 19.2 kcal/mol (Figure 1a) to 24.7 and 44.3 kcal/mol, respectively. For details, see the SI.
-
-
-
-
54
-
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84935007858
-
-
note
-
Substrates with secondary and primary C-H bonds and substrates with aliphatic tethers are unsuccessful. For details, see the SI.
-
-
-
-
55
-
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84935005122
-
-
note
-
The computed activation free energies for the secondary (2-ethyl-N-methoxybenzamide) and primary (2-methyl-N-methoxybenzamide) C-H aminations are 22.4 and 28.5 kcal/mol, much higher than that for the tertiary one (19.2 kcal/mol, Figure 1a). For details, see the SI.
-
-
-
-
56
-
-
84934972517
-
-
note
-
For substrate 1u, the computed activation free energy for the aromatic C-H amination is 1.9 kcal/mol lower than that for the secondary C-H amination. For details, see the SI.
-
-
-
-
57
-
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84934920234
-
-
note
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For the discussion of the radical mechanism, see the SI.
-
-
-
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59
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84935027323
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-
note
-
Geometry optimizations and frequency calculations were performed at the M06-2X/6-31G(d)[SDD, for I] level. Single-point energy calculations in TFE using the CPCM model were performed at the M06-2X/6-311+G(d,p)[SDD, for I] level. For details, see the SI.
-
-
-
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60
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84941083424
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Konnick, M. M.; Hashiguchi, B. G.; Devarajan, D.; Boaz, N. C.; Gunnoe, T. B.; Groves, J. T.; Gunsalus, N.; Ess, D. H.; Periana, R. A. Angew. Chem., Int. Ed. 2014, 53, 10490
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The formation of oxygen-bonded iodonium cation B′ from intermediate A is calculated to be endergonic by 27.9 kcal/mol in TFE.
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84934942757
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For the determination of the absolute configuration, see the SI.
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68
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84934988953
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note
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Under "DFT-computed conditions" [PhI(OAc)2 as oxidant and TFE as solvent], the transformation of (S)-1m to (R)-3m also occurs with complete stereochemical fidelity. For details, see the SI.
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