Metal-free tandem carbene N–H insertions and C–C bond cleavages

Pu Chen; Jiang Nan; Yan Hu; Yifan Kang; Bo Wang; Yangmin Ma; Michal Szostak

doi:10.1039/D0SC05763K

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Metal-free tandem carbene N–H insertions and C–C bond cleavages†

Pu Chen,^a Jiang Nan,

*^a Yan Hu,^a Yifan Kang,^a Bo Wang,^a Yangmin Ma*^a and Michal Szostak

*^ab

Author affiliations

* Corresponding authors

^a Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China
E-mail: nanjiang@sust.edu.cn

^b Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, USA

Abstract

A metal-free C–H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/S_EAr/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids.

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DOI: https://doi.org/10.1039/D0SC05763K
Article type: Edge Article
Submitted: 19 Oct 2020
Accepted: 09 Nov 2020
First published: 10 Nov 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2021,12, 803-811

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Metal-free tandem carbene N–H insertions and C–C bond cleavages

P. Chen, J. Nan, Y. Hu, Y. Kang, B. Wang, Y. Ma and M. Szostak, Chem. Sci., 2021, 12, 803 DOI: 10.1039/D0SC05763K

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Metal-free tandem carbene N–H insertions and C–C bond cleavages†

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Metal-free tandem carbene N–H insertions and C–C bond cleavages

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