Copper-Mediated Nucleophilic Addition/Cascade Cyclization of Aryl Diynes.
Treatment of diyne substrates with sulfinate salts under the action of copper(II) triflate results in a cascade cyclization reaction. The reaction involves nucleophilic addition of the sulfinate and formation of two new C-C bonds with concomitant cleavage of an aryl C-H bond. The reaction proceeds in good yields with a range of diyne precursors and sulfinate salts. Preliminary mechanistic analysis reveals a rare example of an operative ionic mechanism in contrast to other related cyclizations.
Department of Chemistry, University of Waterloo , Waterloo, Ontario N2L 3G1, Canada.
Geoffrey S
GS
Sinclair
Department of Chemistry, University of Waterloo , Waterloo, Ontario N2L 3G1, Canada.
Tianyu
T
Yang
Department of Chemistry, University of Waterloo , Waterloo, Ontario N2L 3G1, Canada.
Sunmeng
S
Wang
Department of Chemistry, University of Waterloo , Waterloo, Ontario N2L 3G1, Canada.
Wei H
WH
Chen
Department of Chemistry, University of Waterloo , Waterloo, Ontario N2L 3G1, Canada.
Derek J
0000-0003-4854-531X
DJ
Schipper