Enantioselective Copper-Catalyzed Remote C(sp(3))-H Alkynylation of Linear Primary Sulfonamides
Organic Letters 22(10):4006-4009 May 2020 

Wang, Cheng-Yu; Qin, Zi-Yang; Huang, Yu-Ling; Hou, Yi-Ming; Jin, Ruo-Xing; Li, Chao; Wang, Xi-Sheng


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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