Organic Chemistry Portal



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:

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


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