Palladium-Catalyzed Arylation of the THP Derivative of (Z)-2-Butene-1,4-diol with Arenediazonium Salts and the Synthesis of β-Aryl-γ-butyrolactones

被引：17
|
作者：
Cacchi, Sandro [1 ]
Fabrizi, Giancarlo [1 ]
Goggiamani, Antonella [1 ]
Sferrazza, Alessio [1 ]
机构：
[1] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
来源：
SYNLETT | 2009年 / 06期
关键词：
arenediazonium salts; palladium; Mizoroki-Heck reaction; tetrahydrofurans; allylic alcohols; CROSS-COUPLING REACTIONS; HECK-TYPE ARYLATION; OVIPOSITION ATTRACTANT PHEROMONE; DIAZONIUM SALTS; STEREOSELECTIVE-SYNTHESIS; ARYLDIAZONIUM SALTS; ALLYLIC ALCOHOLS; CARBOAMINATION REACTIONS; O-BENZENEDISULFONIMIDES; ADDITION-REACTIONS;
D O I：
10.1055/s-0028-1087959
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of arenediazonium tetrafluoroborates with the THP derivative of (Z)-2-butene-1,4-diol in the presence of Pd(OAc)(2) in MeOH at 35 degrees C gives 4-aryl-2-methoxytetrahydrofurans in good to high yields. The reaction tolerates it variety of useful functional groups including ester, keto, cyano. nitro. chloro. and bromo functionalities as well as ortho substituents. Based on this process, gamma-aryl-beta-butyrolactone derivatives can be prepared via a sequential palladium-catalyzed arylation-cyclization-oxidation protocol that omits the isolation of 4-aryl-2-methoxytetrahydrofuran intermediates.
引用
收藏
页码：973 / 977
页数：5
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