Open AccessRegioselective Single-Electron Tsuji–Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach
Author(s) -
Zhengjun Wang,
Shuai Zheng,
Eugénie Romero,
Jennifer K. Matsui,
Gary A. Molander
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02473
Subject(s) - chemistry , allylic rearrangement , electrophile , catalysis , regioselectivity , aryl , alkyl , photoredox catalysis , nickel , combinatorial chemistry , kinetic isotope effect , kinetic resolution , alcohol , photochemistry , catalytic cycle , selectivity , organic chemistry , enantioselective synthesis , deuterium , photocatalysis , physics , quantum mechanics
A radical-mediated functionalization of allyl alcohol derived partners with a variety of alkyl 1,4-dihydropyridines via photoredox/nickel dual catalysis is described. This transformation transpires with high linear and E -selectivity, avoiding the requirement of harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained. Kinetic isotope effect experiments implicated oxidative addition of the nickel catalyst to the allylic electrophile as the turnover-limiting step, supporting previous computational studies.