TY - JOUR
T1 - Copper-Mediated Synthesis of (E)-1-Azido and (Z)-1,2-Diazido Alkenes from 1-Alkene-1,2-diboronic Esters
T2 - An Approach to Mono- And 1,2-Di-(1,2,3-Triazolyl)-Alkenes and Fused Bis-(1,2,3-Triazolo)-Pyrazines
AU - Mali, Maruti
AU - Jayaram, Vankudoth
AU - Sharma, Gangavaram V.M.
AU - Ghosh, Subhash
AU - Berrée, Fabienne
AU - Dorcet, Vincent
AU - Carboni, Bertrand
N1 - Publisher Copyright:
©
PY - 2020/12/4
Y1 - 2020/12/4
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.0c01980
DO - 10.1021/acs.joc.0c01980
M3 - Article
AN - SCOPUS:85096836373
SN - 0022-3263
VL - 85
SP - 15104
EP - 15115
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 23
ER -