Operationally simple copper-promoted coupling of terminal alkynes with benzyl halides.
Benzyl chlorides and bromides are shown to undergo copper-promoted coupling with a variety of terminal alkynes including, for the first time, electron-poor acetylenes such as methyl propiolate. The reaction permits easy access to a wide range of (functionalized) benzyl-substituted propiolates (as well as several related alkynes) from commercially available benzyl halides. These products should in turn function as useful building blocks for the synthesis of previously inaccessible (functionalized) benzyl-substituted heterocycles.
Davies
Katherine A
KA
Department of Chemistry, University of Victoria, Victoria, British Columbia, Canada, V8W 3V6.
Abel
Ryan C
RC
Wulff
Jeremy E
JE
D000480:Alkynes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry
D000480:Alkynes; D001593:Benzyl Compounds; D006219:Halogens; D006571:Heterocyclic Compounds; D003300:Copper