Construction of N-Acyliminophosphoranes via Iron(II)-Catalyzed Imidization of Phosphines with N-Acyloxyamides

Sen Lin, Bo Lin, Zongtao Zhang, Jianhui Chen*, Yanshu Luo and Yuanzhi Xia*

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China, Email: cjhwzu.edu.cn, xyzwzu.edu.cn

S. Lin, B. Lin, Z. Zhang, J. Chen, Y. Luo, Y. Xia, Org. Lett., 2022, 24, 3302-3306.

DOI: 10.1021/acs.orglett.2c01238

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Abstract

FeCl₂ catalyzes a facile imidization of phosphines with N-acyloxyamides to provide synthetically useful N-acyliminophosphoranes with high functional group tolerance. The transformation can be scaled up to gram scale with a catalyst loading of 1 mol%. The iminophosphoranyl moiety is an effective directing group for Rh(III)-catalyzed ortho C(sp2)-H bond amidations.

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Key Words

iminophosphoranes

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ID: J54-Y2022