Issue 22, 2021

Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides

Abstract

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities. The reaction is tolerant of a variety of functional groups, and the resulting products can be converted to pharmaceutically-relevant chiral building blocks. A multivariate linear regression model was developed to quantitatively relate the influence of the α-chloroester substrate and ligand on enantioselectivity.

Graphical abstract: Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides

Supplementary files

Article information

Article type
Edge Article
Submitted
09 feb 2021
Accepted
24 apr 2021
First published
26 apr 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 7758-7762

Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides

T. J. DeLano, S. E. Dibrell, C. R. Lacker, A. R. Pancoast, K. E. Poremba, L. Cleary, M. S. Sigman and S. E. Reisman, Chem. Sci., 2021, 12, 7758 DOI: 10.1039/D1SC00822F

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