Реферат: Combined density functional and ONIOM studies have been performed to investigate the mechanism of rhodium-catalyzed boration of imines. Catalytic imine boration has been found to proceed via the following stages:  (1) oxidative addition of B−B to the Rh complex, (2) imine coordination, (3) migratory insertion of the imine into the rhodium−boron (Rh−B) bond, and (4) β-hydrogen elimination to give a monoboration product or carbon−boron (C−B) bond formation to yield a diboration product. The choice of the final stage depends on the structure of the imine and boration reagent. Bulky substrate molecules facilitate C−H bond activation and retard C−B bond formation, while in the absence of sterical hindrance C−B bond formation is preferred over C−H bond activation. The present study is the first that outlines the mechanistic differences in CC and CN bond boration and rationalizes the effect of bulky substituents on the mechanism of imine boration reaction. The expected difference in regioselectivity between imine and alkene boration is also discussed.

Библиографическая ссылка: Ananikov V.P. , Szilagyi R. , Morokuma K. , Musaev D.G.
Can Steric Effects Induce the Mechanism Switch in the Rhodium-Catalyzed Imine Boration Reaction? A Density Functional and ONIOM Study
Organometallics. 2005. V.24. N8. P.1938-1946. DOI: 10.1021/om049156o WOS Scopus OpenAlex

Идентификаторы БД:

Web of science:	WOS:000228191400021
Scopus:	2-s2.0-17244362411
OpenAlex:	W2086897548

Цитирование в БД:

БД	Цитирований
OpenAlex	35
Scopus	38
Web of science	34

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