School of Chemistry &
Chemical Engineering, South China University
of Technology, Wushan
Road - 381, Guangzhou 510641, People’s Republic of China
Chemical Engineering, South China University
of Technology, Wushan
Road - 381, Guangzhou 510641, People’s Republic of China
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.6b01390
Publication Date (Web): June 14, 2016
Copyright © 2016 American Chemical Society
Abstract
A
new benzylation protocol, enabling straightforward access to
β-benzylated quinolines, has been demonstrated. By employing readily
available [RuCl2(p-cymene)]2 as a catalyst and O2
as a sole green oxidant, various 1,2,3,4-tetrahydroquinolines were
efficiently converted in combination with aryl aldehydes into desired
products in a step- and atom-economic fashion together with the
advantages of excellent functional group tolerance and chemoselectivity,
offering an important basis for the transformation of saturated N-heterocycles into functionalized N-heteroaromatics
via a dehydrogenative cross-coupling strategy. Mechanistic
investigations support that the reaction undergoes a
monodehydrogenation-triggered β-benzylation mode.
new benzylation protocol, enabling straightforward access to
β-benzylated quinolines, has been demonstrated. By employing readily
available [RuCl2(p-cymene)]2 as a catalyst and O2
as a sole green oxidant, various 1,2,3,4-tetrahydroquinolines were
efficiently converted in combination with aryl aldehydes into desired
products in a step- and atom-economic fashion together with the
advantages of excellent functional group tolerance and chemoselectivity,
offering an important basis for the transformation of saturated N-heterocycles into functionalized N-heteroaromatics
via a dehydrogenative cross-coupling strategy. Mechanistic
investigations support that the reaction undergoes a
monodehydrogenation-triggered β-benzylation mode.
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