Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of Trialkylboranes with Aryl Bromides in the Presence of Unmasked Acidic or Basic Functions and Base-Labile Protections under Mild Non-Aqueous Conditions

被引：22
作者：
Wang, Bing [1 ]
Sun, Hui-Xia [1 ]
Sun, Zhi-Hua [2 ]
Lin, Guo-Qiang [1 ,3 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Shanghai Saijia Chem Co Ltd, Shanghai 200232, Peoples R China
[3] Fudan Univ, Inst Biomed Sci, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 03期
基金：
中国国家自然科学基金;
关键词：
alkylation; boranes; cross-coupling; palladium; Suzuki-Miyaura reaction; ASYMMETRIC-SYNTHESIS; ARYLBORONIC ACIDS; CESIUM CARBONATE; BOND; DERIVATIVES; ESTERS; REAGENTS; CLEAVAGE;
D O I：
10.1002/adsc.200800630
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient and chemoselective palladium-catalyzed direct B-alkyl Suzuki-Miyaura cross-coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non-aqueous conditions are compatible with aldehydes, ketones, nitriles, chloro substitution as well as base-labile phenolic Piv and TBS protecting groups. The anhydrous conditions were found to be advantageous for aryl bromide substrates. A potent CEPT inhibitor was efficiently synthesised using this protocol.
引用
收藏
页码：415 / 422
页数：8
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