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Dioxygen-Triggered Oxidative Radical Reaction: Direct Aerobic Difunctionalization of Terminal Alkynes toward β-Keto Sulfones

Qingquan Lu, Jian Zhang, Ganglu Zhao, Yue Qi, Huamin Wang and Aiwen Lei*

*College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China, Email: aiwenleiwhu.edu.cn

Q. Lu, J. Zhang, G. Zhao, Y. Qi, H. Wang, A. Lei, J. Am. Chem. Soc., 2013, 135, 11481-11484.

DOI: 10.1021/ja4052685 (free Supporting Information)


Abstract

In an unprecedented oxidative radical process, dioxygen as the solely terminal oxidant triggers an aerobic oxidative difunctionalization of terminal alkynes toward β-keto sulfones with high selectivity. IR experiments revealed that pyridine not only acts as a base to successfully surpress ATRA (atom transfer radical addition) process, but also plays a vital role in reducing the activity of sulfinic acids.

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Key Words

sulfones, oxygen


ID: J48-Y2013