Direct vinylation and difluorovinylation of arylboronic acids using vinyl- and 2,2-difluorovinyl tosylates via the Suzuki-Miyaura cross coupling

被引:107
作者
Gogsig, Thomas M. [1 ]
Sobjerg, Lina S. [1 ]
Lindhardt , Anders T. [1 ]
Jensen, Kim L. [1 ]
Skrydstrup, Troels [1 ]
机构
[1] Univ Aarhus, Dept Chem & Insterdisciplinary Nanosci Ctr, Ctr Insoluble Prot Struct inSPIN, DK-8000 Aarhus, Denmark
关键词
D O I
10.1021/jo7027097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
General reaction conditions were developed for the Pd(0)-catalyzed Suzuki-Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded to provide a facile and straightforward approach for the introduction of a gem-difluorovinyl substituent onto an aromatic ring using the similar and also readily available 2,2-difluorovinyl tosylate as the electrophilic complement.
引用
收藏
页码:3404 / 3410
页数:7
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