Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents

Jianming Yan, Haidi Tang, Eugene Jun Rong Kuek, Xiangcheng Shi, Chenguang Liu, Muliang Zhang (), Jared L. Piper, Shengquan Duan () and Jie Wu ()
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Jianming Yan: National University of Singapore
Haidi Tang: National University of Singapore
Eugene Jun Rong Kuek: National University of Singapore
Xiangcheng Shi: National University of Singapore
Chenguang Liu: National University of Singapore
Muliang Zhang: National University of Singapore
Jared L. Piper: Pfizer Worldwide Research and Development
Shengquan Duan: Pfizer Worldwide Research and Development
Jie Wu: National University of Singapore

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract While aldehydes represent a classic class of electrophilic synthons, the corresponding acyl radicals are inherently nucleophilic, which exhibits umpolung reactivity. Generation of acyl radicals typically requires noble metal catalysts or excess oxidants to be added. Herein, we report a convenient and green approach to access acyl radicals, capitalizing on neutral eosin Y-enabled hydrogen atom transfer (HAT) photocatalysis with aldehydes. The generated acyl radicals underwent SOMOphilic substitutions with various functionalized sulfones (X–SO2R’) to deliver value-added acyl products. The merger of eosin Y photocatalysis and sulfone-based SOMOphiles provides a versatile platform for a wide array of aldehydic C–H functionalizations, including fluoromethylthiolation, arylthiolation, alkynylation, alkenylation and azidation. The present protocol features green characteristics, such as being free of metals, harmful oxidants and additives; step-economic; redox-neutral; and amenable to scale-up assisted by continuous-flow technology.

Date: 2021
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DOI: 10.1038/s41467-021-27550-8

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