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Intramolecular Csp 3 -H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines.

Authors :
Wen X
Li X
Luo X
Wang W
Song S
Jiao N
Source :
Chemical science [Chem Sci] 2020 Apr 07; Vol. 11 (17), pp. 4482-4487. Date of Electronic Publication: 2020 Apr 07.
Publication Year :
2020

Abstract

The intramolecular Csp <superscript>3</superscript> -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 Csp <superscript>3</superscript> -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.<br />Competing Interests: There are no conflicts to declare.<br /> (This journal is © The Royal Society of Chemistry.)

Details

Language :
English
ISSN :
2041-6520
Volume :
11
Issue :
17
Database :
MEDLINE
Journal :
Chemical science
Publication Type :
Academic Journal
Accession number :
34122906
Full Text :
https://doi.org/10.1039/c9sc05522c