Enantioselective Reductive (Hetero)Arylation of Cyclic N-Sulfonyl Imines by Cobalt Catalysis

Jieshuai Xiao; Minyan Wang; Xuwen Yin; Shuo Yang; Pei Gu; Xueli Lv; Yue Zhao; Zhuangzhi Shi

doi:10.1002/anie.202300743

Enantioselective Reductive (Hetero)Arylation of Cyclic N-Sulfonyl Imines by Cobalt Catalysis

Angew Chem Int Ed Engl. 2023 May 2;62(19):e202300743. doi: 10.1002/anie.202300743. Epub 2023 Mar 30.

Authors

Jieshuai Xiao¹, Minyan Wang¹, Xuwen Yin¹, Shuo Yang¹, Pei Gu¹, Xueli Lv¹, Yue Zhao¹, Zhuangzhi Shi^{1

2

3}

Affiliations

¹ State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
² College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002, China.
³ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007, China.

PMID: 36916783
DOI: 10.1002/anie.202300743

Abstract

Transition-metal-catalyzed enantioselective addition of aryl organometallic reagents to imines has emerged as one of the most powerful tools for the formation of optically active diarylmethylamines. Here, we report the first asymmetric reductive (hetero)arylations of imines using aryl and heteroaryl halides enabled by a chiral cobalt-bisphosphine catalyst. This approach shows good functional group compatibility and complements the reported strategy without use of organometallic reagents. Mechanistic investigations supported that aryl-cobalt, instead of an arylzinc reagent, was formed in situ in this reductive aryl-addition event.

Keywords: Addition; Arylation; Cobalt; Enantioselectivity; Imines.

Abstract

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