Chinese Journal of Organic Chemistry >
Copper-Catalyzed Regioselective C(sp3)—H Sulfonimidization of Aliphatic Cyclic Tertiary Amines
Received date: 2021-06-21
Revised date: 2021-07-17
Online published: 2021-07-26
Supported by
Chongqing Municipal Education Commission(CXQT20026); Basic Research and Frontier Exploration of Science and Technology Commission of Chongqing(cstc2019jcyj-msxm1275); Fuling District Science and Technology(FLKJ); Fuling District Science and Technology(2019ABB2038); Science and Technology Research Program of Chongqing Municipal Education Commission(KJQN202001403)
This paper reports a concise and efficient synthesis method, namely copper-catalyzed direct hydrocarbon dehydrogenation coupling of sulfonamides and aliphatic cyclic tertiary amines, to realize the highly regioselective synthesis of (E)-N-sulfonylformamidines. The reaction is accomplished without any corrosive acid or base as an additive. It tolerates a broad scope of substrates, good functional group compatibility, and generates exclusive (E)-stereoselectivity. Moreover, this utility of the protocol is successfully demonstrated in a late-stage functionalization of medicinally active molecules and gram-scale synthesis.
Quan Gou , Qiujian Tan , Qianqiong Chen , Jianhong Tan , Kaimin Wang , Jianfeng Xie . Copper-Catalyzed Regioselective C(sp3)—H Sulfonimidization of Aliphatic Cyclic Tertiary Amines[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4459 -4466 . DOI: 10.6023/cjoc202106035
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