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Photoinduced, Copper-Catalyzed Enantioconvergent Alkylations of Anilines by Racemic Tertiary Electrophiles: Synthesis and Mechanism

Hyungdo Cho, Hidehiro Suematsu, Paul H. Oyala, Jonas C. Peters* and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: jpeterscaltech.edu, gcfucaltech.edu

H. Cho, H. Suematsu, P. H. Oyala, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2022, 144, 4550-4558.

DOI: 10.1021/jacs.1c12749


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Abstract

A readily accessible chiral copper catalyst can achieve a photoinduced, enantioconvergent coupling of a variety of racemic tertiary alkyl electrophiles with aniline nucleophiles to generate a new C-N bond with good ee at the fully substituted stereocenter of the product.


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proposed mechanism

(R)-DTBM-SEGPHOS / BTPP



Key Words

α-amino nitriles, photochemistry


ID: J48-Y2022