Open AccessRuthenium-Catalyzed C–H Allylation of Alkenes with Allyl Alcohols via C–H Bond Activation in Aqueous Solution
Author(s) -
Xiaowei Wu,
Haitao Ji
Publication year - 2018
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.8b02063
Subject(s) - chemistry , ruthenium , catalysis , aqueous solution , bond cleavage , stereoselectivity , medicinal chemistry , substrate (aquarium) , alkene , organic chemistry , oceanography , geology
A robust Ru(II)-catalyzed C-H allylation of electron-deficient alkenes with allyl alcohols in aqueous solution is reported. This method provides a straightforward and efficient access to the synthetically useful 1,4-diene skeletons. With the assistance of the N-methoxycarbamoyl directing group, this allylation reaction features a broad substrate scope with good functional group tolerance, excellent regio- and stereoselectivity, absence of metal oxidants, water-tolerant solvents, and mild reaction conditions. The mechanistic studies indicate that the process of the reversible C-H bond ruthenation is assisted by acetate, and the rate-determining step is unlikely to be the step of C-H bond cleavage.