Heck vinylations using vinyl sulfide, vinyl sulfoxide, vinyl sulfone, or vinyl sulfonate derivatives and aryl bromides catalyzed by a palladium complex derived from a tetraphosphine

被引:48
作者
Battace, Ahmed
Zair, Touriya
Doucet, Henri
Santelli, Maurice
机构
[1] Univ Aix Marseille 3, Fac Sci St Jerome, CNRS, UMR 6180,Lab Synth Organ, F-13397 Marseille 20, France
[2] Univ Moulay Ismail, Fac Sci, Lab Chim Organ Appl, Meknes 50000, Morocco
来源
SYNTHESIS-STUTTGART | 2006年 / 20卷 / 20期
关键词
Heck reaction; palladium; phosphine; vinylsulfur; catalyst;
D O I
10.1055/s-2006-950244
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The adverse impact of sulfur compounds on catalytic performance is well known. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino)methyl]cyclopentane in combination with allylchloropalladium dimer affords an efficient catalyst for the Heck reaction of sulfur-containing alkenes with aryl bromides. The rates and yields of the reactions strongly depend on the oxidation state of the sulfur atom. Using vinyl sulfides with 1 mol% catalyst, low to moderate yields of arylated alkenes were obtained. Phenyl vinyl sulfoxide was found to be more reactive, and satisfactory yields of (E)-[2-(phenyisulfinyl)vinyl]benzene derivatives were obtained using I mol% catalyst. With methyl vinyl sulfone, very high yields of (E)- [2-(methyl sulfonyl)vinyl] benzene derivatives were obtained using 1-0. 1 mol% catalyst. Phenyl vinyl sulfonie and phenyl vinylsulfonate also gave high yields of the expected products, but in the presence of 0.4-1 mol% catalyst.
引用
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页码:3495 / 3505
页数:11
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