Journal
ACS CATALYSIS
Volume 5, Issue 2, Pages 587-595Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs501924c
Keywords
heterogeneous reaction; Rh(I) catalysis; C-H activation; cyclometalation; direct alkylation; kinetic isotope effects; reaction mechanism
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Funding
- Austrian Science Foundation (FWF) [P21202-N17]
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Mechanistic investigations of a Rh(I)-catalyzed direct C-H alkylation of benzyhc amines with alkenes, formally an C(sp(3))-H activation, reveal this reaction to proceed via imine intermediates and, hence, via C(sp(2))-H activation. The reaction shows a primary kinetic isotope effect of 4.3 at the benzylic C-H position together with a reversible H-D exchange at the same position, which indicates that there are at least two distinct steps in which the corresponding C-H bonds are broken. The imine intermediates are shown to be converted to the final product under the reaction conditions, and a time course analysis of the alkylated imine intermediate shows that it is formed before the final amine product in the course of the reaction.
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