Synthesis of 1,3-diynes via palladium-catalyzed reaction of 1,1-dibromo-1-alkenes

被引:90
作者
Shen, W [1 ]
Thomas, SA [1 ]
机构
[1] Abbott Labs, Div Pharmaceut Prod, Dept D4N6, Abbott Pk, IL 60064 USA
关键词
D O I
10.1021/ol006282p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both symmetric and unsymmetric 1,3-diynes were prepared from the palladium-catalyzed reaction of 1,l-dibromo-l-alkenes. The formation of symmetric 1,3-diynes 2 (homocoupling) was catalyzed by a weak ligand, tris(2-furyl)phosphine (TFP), and the addition of catalytic amount of Cul accelerated the reaction. The synthesis of unsymmetric 1,3-diynes 4 (the Sonogashira reaction) required a highly electron rich tris(4-methoxyphenyl)phosphine as the ligand, and Cul promotes the formation of byproduct 1,1-diynyl-1-alkenes 5.
引用
收藏
页码:2857 / 2860
页数:4
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