Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations

Manman Sun; Weida Chen; Xiangyu Xia; Guodong Shen; Yongmin Ma; Jianguo Yang; Hanfeng Ding; Zhiming Wang

doi:10.1021/acs.orglett.0c01011

Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations

Org Lett. 2020 Apr 17;22(8):3229-3233. doi: 10.1021/acs.orglett.0c01011. Epub 2020 Mar 27.

Authors

Manman Sun¹, Weida Chen¹, Xiangyu Xia¹, Guodong Shen², Yongmin Ma¹, Jianguo Yang¹, Hanfeng Ding³, Zhiming Wang¹

Affiliations

¹ Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, P. R. China.
² School of Chemistry and Chemical Engineering, School of Pharmacy, Liaocheng University, Liaocheng 252000, P. R. China.
³ Department of Chemistry, Zhejiang University, Hangzhou 310058, P. R. China.

PMID: 32216363
DOI: 10.1021/acs.orglett.0c01011

Abstract

A palladium-catalyzed tandem dehydrogenative [4 + 2] annulation of terminal olefins with N-sulfonyl amides via C(sp²)-H activation, allylic C(sp³)-H activation, and homoallylic C(sp³)-H elimination processes has been developed. Promoted by the DMSO ligand, various benzamides, heterocyclic arylamides, alkenyl carboxamides, and commercial olefins are found to be efficient substrates to construct important heterocyclic compounds bearing a vinyl substituent with high E stereoselectivity. Using air as the terminal oxidant also provides a great advantage regarding environmental friendliness.