The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes:: Synthesis of (E)-1-tributylstannyl-1-alkenes

被引:71
作者
Darwish, Alla [1 ]
Lang, Adam [1 ]
Kim, Thomas [1 ]
Chong, J. Michael [1 ]
机构
[1] Univ Waterloo, Dept Chem, Guelph Waterloo Program Grad Work Chem & Biochem, Waterloo, ON N2L 3G1, Canada
关键词
D O I
10.1021/ol702982x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regiochemistry of palladium-catalyzed hydrostannations of terminal alkynes is dramatically influenced by ligand effects. Use of phosphines such as Cy(3)P, t-Bu(2)PCH(2)t-Bu, and t-Bu(3)P provides (E)-1-tributylstannyl-1-alkenes with regioselectivities up to > 99:< 1 for substrates where the commonly used Ph(3)P shows much lower regioselectivities.
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页码:861 / 864
页数:4
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