Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 12, Pages 3654-3661Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob02064b
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Funding
- National Natural Science Foundation of China [21173126, 21303073, 21473100]
- Natural Science Foundation of Shandong Province [ZR2013BL005, ZR2014BL013]
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A density functional theory study was performed to understand the detailed mechanisms of the cross-benzoin reactions catalyzed by N-heterocyclic carbene (NHC) species. Our theoretical study predicted that the first H-transfer operates with water in solution as a mediator, and the second H-transfer undergoes a concerted mechanism rather than a stepwise one. In addition, the chemoselectivity of the reactions studied in this work has been explored. P1 was obtained as a major product mainly due to the more stable intermediate formed by reaction of NHC with reactant R1. Different steric effects resulting from the fused six-membered ring in transition state TS7 and the fused five-membered ring in transition state TS13 are the origin leading to the chemoselectivity.
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