Issue 17, 2020

Intramolecular Csp3–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

Abstract

The intramolecular Csp3–H and/or C–C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp3–H and/or C–C bond cleavage. Two C–N single bonds or a C[double bond, length as m-dash]N double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.

Graphical abstract: Intramolecular Csp3–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

Supplementary files

Article information

Article type
Edge Article
Submitted
31 10 2019
Accepted
07 4 2020
First published
07 4 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 4482-4487

Intramolecular Csp3–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

X. Wen, X. Li, X. Luo, W. Wang, S. Song and N. Jiao, Chem. Sci., 2020, 11, 4482 DOI: 10.1039/C9SC05522C

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