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

Maruti Mali; Vankudoth Jayaram; Gangavaram V M Sharma; Subhash Ghosh; Fabienne Berrée; Vincent Dorcet; Bertrand Carboni

doi:10.1021/acs.joc.0c01980

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

J Org Chem. 2020 Dec 4;85(23):15104-15115. doi: 10.1021/acs.joc.0c01980. Epub 2020 Nov 5.

Authors

Maruti Mali¹, Vankudoth Jayaram¹, Gangavaram V M Sharma¹, Subhash Ghosh^{1

2}, Fabienne Berrée³, Vincent Dorcet³, Bertrand Carboni³

Affiliations

¹ Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
² Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
³ Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France.

PMID: 33151061
DOI: 10.1021/acs.joc.0c01980

Abstract

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.