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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.
- 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