Copper-Mediated Synthesis of (E)‑1-Azido and (Z)‑1,2-Diazido Alkenes from 1‑Alkene-1,2-diboronic Esters: An Approach to Mono- and 1,2-Di-(1,2,3-Triazolyl)-Alkenes and Fused Bis-(1,2,3-Triazolo)-Pyrazines

A stereoselective and convenient route has been demonstrated to access (Z)-1,2-diazido alkenes from the corresponding 1,2-diboronic esters via a copper-mediated reaction with sodium azide. Alternately, mono-functionalization was regioselectively carried out with trimethylsilyl azide as an azidation...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-12, Vol.85 (23), p.15104-15115
Main Authors: Mali, Maruti, Jayaram, Vankudoth, Sharma, Gangavaram V. M, Ghosh, Subhash, Berrée, Fabienne, Dorcet, Vincent, Carboni, Bertrand
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:A stereoselective and convenient route has been demonstrated to access (Z)-1,2-diazido alkenes from the corresponding 1,2-diboronic esters via a copper-mediated reaction with sodium azide. Alternately, mono-functionalization was regioselectively carried out with trimethylsilyl azide as an azidation reactant. The in situ conversion of bis-azides to the corresponding bis-triazoles can be readily achieved in the presence of copper sulfate and sodium ascorbate, while the modification of the catalytic system opened a new convenient route to bis-triazolo-pyrazines, a new class of fused heterocycles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01980