TY - JOUR
T1 - Copper(i)-catalyzed cycloaddition of silver acetylides and azides
T2 - Incorporation of volatile acetylenes into the triazole core
AU - Proietti Silvestri, Ilaria
AU - Andemarian, Fikre
AU - Khairallah, George N.
AU - Wan Yap, Su
AU - Quach, Tim
AU - Tsegay, Sammi
AU - Williams, Craig M
AU - O'Hair, Richard Alfred John
AU - Donnelly, Paul Stephen
AU - Williams, Spencer John
PY - 2011/9/7
Y1 - 2011/9/7
N2 - Silver acetylides and organic azides react under copper(i) catalysis to afford 1,4-disubstituted 1,2,3-triazoles. Mechanistic studies implicate a process involving transmetallation to copper acetylides prior to cycloaddition. This work demonstrates that silver acetylides serve as suitable precursors for entry into copper-mediated coupling reactions. This methodology allows the incorporation of volatile and difficult-to-handle acetylenes into the triazole core.
AB - Silver acetylides and organic azides react under copper(i) catalysis to afford 1,4-disubstituted 1,2,3-triazoles. Mechanistic studies implicate a process involving transmetallation to copper acetylides prior to cycloaddition. This work demonstrates that silver acetylides serve as suitable precursors for entry into copper-mediated coupling reactions. This methodology allows the incorporation of volatile and difficult-to-handle acetylenes into the triazole core.
UR - http://www.scopus.com/inward/record.url?scp=80052064289&partnerID=8YFLogxK
U2 - 10.1039/c1ob05360d
DO - 10.1039/c1ob05360d
M3 - Article
C2 - 21748192
AN - SCOPUS:80052064289
SN - 1477-0520
VL - 9
SP - 6082
EP - 6088
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
IS - 17
ER -