Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach
Zheng-Jun Wang, Shuai Zheng, Eugénie Romero, Jennifer K. Matsui, Gary A. Molander*
*Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States,
Email: gmolandr
sas.upenn.edu
Z.-J. Wang, S. Zheng, E. Romero, J. K. Matsui, G. A. Molander, Org. Lett., 2019, 21, 6543-6547.
DOI: 10.1021/acs.orglett.9b02473
see article for more reactions
Abstract
Photoredox/nickel dual catalysis enables a radical-mediated functionalization of allyl alcohol (derivatives) with a variety of alkyl 1,4-dihydropyridines with high linear and E-selectivity. This reaction avoids harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained.
see article for more examples
proposed mechanism
Key Words
allylation, Tsuji-Trost reaction, photochemistry
ID: J54-Y2019
