Palladium-Catalyzed Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Organic Halides in Aqueous Media

被引：58

作者：

Alacid, Emilio ^{[1
,2
]}

Najera, Carmen ^{[1
,2
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

[2] Univ Alicante, Inst Sintesis Organ, Alicante 03080, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 06期

关键词：

ARYL BROMIDES; VINYLATION; CHLORIDES; ALKENYL; ACIDS; VINYLTRIFLUOROBORATE; PERSPECTIVES; REAGENTS; ALCOHOLS; STYRENES;

D O I：

10.1021/jo802356n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Potassium vinyl and alkenyltrifluoroborates are cross-coupled with aryl and heteroaryl bromides using 1 mol % Pd loading of 4-hydroxyacetophenone oxime derived palladacycle or Pd(OAc)(2) as precatalysts, K2CO3 as base, and TBAB as additive and water reflux under conventional or microwave heating to afford styrenes, stilbenoids, and alkenyl benzenes. These borates can be cross-coupled diastereoselectively with allyl and benzyl chlorides using KOH as base in acetone-water (3:2) at 50 degrees C and 0.1 mol % Pd loading, giving the corresponding 1,4-dienes and allylarenes, respectively. These simple phosphine-free reaction conditions allow the palladium recycling from the aqueous phase during up to five runs by extractive separation of the products, which contain 58-105 ppm of Pd.

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页码：2321 / 2327

页数：7

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