Synthesis of δ-Bromo γ,δ-Unsaturated Carbonyl Compounds via Palladium-Catalyzed Bromoalkylation of Alkynoates

被引：37
|
作者：
Wen, Yanmei [1 ,2 ]
Huang, Liangbin [1 ]
Jiang, Huanfeng [1 ]
Chen, Huoji [1 ]
机构：
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
[2] Guangdong Ocean Univ, Coll Sci, Zhanjiang 524088, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 04期
基金：
中国国家自然科学基金;
关键词：
BETA-HETEROATOM ELIMINATION; ALLYL ALCOHOLS; RECONSTITUTIVE CONDENSATION; (Z)-4'-ACETOXY-2'-BUTENYL 2-ALKYNOATES; PALLADIUM(II)-CATALYZED CYCLIZATION; PROPARGYL ALCOHOLS; MOLECULAR-OXYGEN; BOND FORMATION; AQUEOUS-MEDIA; ALKYNES;
D O I：
10.1021/jo202416h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed regio- and stereoselective intermolecular tandem reaction of electron-deficient alkynes, CuBr2, and allylic alcohol to synthesize delta-bromo-gamma,delta-unsaturated carbonyls was developed. A mechanism involving bromopalladation of alkyne, followed by insertion of allylic alcohol and allylic hydrogen shift, is proposed. The shift of allylic hydrogen is the rate-limiting step in this reaction.
引用
收藏
页码：2029 / 2034
页数：6
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