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Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox Catalysis

Guang-Zu Wang, Rui Shang*, Wan-Min Cheng and Yao Fu*

*Department of Chemistry, University of Science and Technology of China, Hefei 230026, P.R. China, Email: faint123mail.ustc.edu.cn, fuyaoustc.edu.cn

G.-Z. Wang, R. Shang, W.-M. Cheng, Y. Fu, Org. Lett., 2015, 17, 4830-4833.

DOI: 10.1021/acs.orglett.5b02392


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Abstract

Iridium photoredox catalysis enables a decarboxylative 1,4-addition of 2-oxo-2-(hetero)arylacetic acids to various Michael acceptors including α,β-unsaturated ester, ketone, amide, aldehyde, nitrile, and sulfone at room temperature. 2-Oxo-2-(hetero)arylacetic acids are easily accessible precursors of acyl anions through photoredox-catalyzed radical decarboxylation.


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iridium photoredox catalyst



Key Words

1,4-ketoesters, 1,4-diketones


ID: J54-Y2015