ORGANIC LETTERS
The Use of Phosphine Ligands to Control the Regiochemistry of Pd-Catalyzed Hydrostannations of 1-Alkynes: Synthesis of (E)-1-Tributylstannyl-1-alkenes
2008 Vol. 10, No. 5 861-864
Alla Darwish, Adam Lang, Thomas Kim, and J. Michael Chong* Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry (GWC)2, Department of Chemistry, UniVersity of Waterloo, Waterloo, Ontario, Canada N2L 3G1
[email protected] Received December 11, 2007
ABSTRACT
The regiochemistry of palladium-catalyzed hydrostannations of terminal alkynes is dramatically influenced by ligand effects. Use of phosphines such as Cy3P, t-Bu2PCH2t-Bu, and t-Bu3P provides (E)-1-tributylstannyl-1-alkenes with regioselectivities up to >99:
