Stereo- and regioselective palladium-catalysed hydroarylation and hydrovinylation of functionalised alkynes: a route to substituted Z-2-cinnamyl esters, 3-chromen-2-ols, and coumarins

被引：0

作者：

Cacchi, S ^{[1
]}

Fabrizi, G ^{[1
]}

Moro, L ^{[1
]}

Pace, P ^{[1
]}

机构：

[1] Univ Rome La Sapienza, Dipartimento Studi Chim & Technol Sostanze Biol A, I-00185 Rome, Italy

来源：

SYNLETT | 1997年 / 12期

关键词：

palladium; hydroarylation; hydrovinylation; cyclization; cinnamyl esters; chromenols; coumarins;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalysed hydroarylation and hydrovinylation of methyl 3-phenylpropynoate and 3,3-diethoxy-1-(o-tetrahydropyranyloxy)phenyl-1-propyne with aryl and vinyl halides or triflates in the presence of Pd(OAc)(2) and KOOCH has been studied. The reaction affords stereoselectively syn addition products. The regiochemical outcome appears to be controlled by steric effects and the new carbon-carbon bond is generated preferentially on the carbon far from the aromatic ring ligated to the acetylenic carbon. The reaction can be applied to the synthesis of 3-substituted-3-chromen-2-ols and 3-substituted coumarins.

引用

页码：1367 / 1370

页数：4