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Enantioselective Copper-Catalyzed Remote C(sp3)-H Alkynylation of Linear Primary Sulfonamides
Cheng-Yu Wang1, Zi-Yang Qin1, Yu-Ling Huang1
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, Center for Excellence in Molecular Synthesis of CAS, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
Abstract:
The highly efficient copper-catalyzed enantioselective alkynylation of the remote C(sp3)-H bond on linear primary sulfonamides is presented here using a radical relay strategy. The chiral box-copper complex, which is used to recapture the in-situ-generated alkyl radical via a 1,5-HAT strategy, is the key to success, affording the chiral alkynes after a following reductive elimination. A general substrate scope, mild conditions, and excellent regio- and enantioselective control are demonstrated in this method.
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