Enantioselective Radical Construction of 5‑Membered Cyclic Sulfonamides by Metalloradical C–H Amination

Both arylsulfonyl and alkylsulfonyl azides can be effectively activated by the cobalt(II) complexes of D 2-symmetric chiral amidoporphyrins for enantioselective radical 1,5-C–H amination to stereoselectively construct 5-membered cyclic sulfonamides. In addition to C–H bonds with varied electronic p...

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Bibliographic Details
Published in:	Journal of the American Chemical Society 2019-11, Vol.141 (45), p.18160-18169
Main Authors:	Hu, Yang, Lang, Kai, Li, Chaoqun, Gill, Joseph B, Kim, Isaac, Lu, Hongjian, Fields, Kimberly B, Marshall, McKenzie, Cheng, Qigan, Cui, Xin, Wojtas, Lukasz, Zhang, X. Peter
Format:	Article
Language:	eng
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Summary:	Both arylsulfonyl and alkylsulfonyl azides can be effectively activated by the cobalt(II) complexes of D 2-symmetric chiral amidoporphyrins for enantioselective radical 1,5-C–H amination to stereoselectively construct 5-membered cyclic sulfonamides. In addition to C–H bonds with varied electronic properties, the Co(II)-based metalloradical system features chemoselective amination of allylic C–H bonds and is compatible with heteroaryl groups, producing functionalized 5-membered chiral cyclic sulfonamides in high yields with high enantioselectivities. The unique profile of reactivity and selectivity of the Co(II)-catalyzed C–H amination is attributed to its underlying stepwise radical mechanism, which is supported by several lines of experimental evidence.
ISSN:	0002-7863 1520-5126