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Merging of Light/Dark Palladium Catalytic Cycles Enables Multicomponent Tandem Alkyl Heck/Tsuji-Trost Homologative Amination Reaction toward Allylic Amines

Nikita Kvasovs, Jian Fang, Fedor Kliuev and Vladimir Gevorgyan*

*Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, Texas 75080-3021, United States, Email:

N. Kvasovs, J. Fang, F. Kliuev, V. Gevorgyan, J. Am. Chem. Soc., 2023, 145, 18497-18505.

DOI: 10.1021/jacs.3c04968

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A visible light-induced palladium-catalyzed homologative three-component synthesis of a broad range of allylic amines involves two distinct cycles enabled by the same Pd(0) catalyst: a visible light-induced hybrid radical alkyl Heck reaction between 1,1-dielectrophile and styrene, followed by the "in dark" classical Tsuji-Trost-type allylic substitution reaction.

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proposed mechanism

Key Words

Heck reaction, Tsuji-Trost allylation, allylic amines, photochemistry, multicomponent reactions

ID: J48-Y2023