Suzuki-Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs

被引:35
|
作者
Fleury-Bregeot, Nicolas [2 ]
Presset, Marc [1 ]
Beaumard, Floriane [2 ]
Colornbel, Virginie [1 ]
Oehlrich, Daniel [1 ]
Rombouts, Frederik [1 ]
Molander, Gary A. [2 ]
机构
[1] Janssen Pharmaceut, Res & Dev, Neurosci Med Chem, B-2340 Beerse, Belgium
[2] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期
基金
美国国家科学基金会;
关键词
BOC-PROTECTED AMINOMETHYLTRIFLUOROBORATE; C-H BONDS; CATALYZED BORYLATION; ALKYL-HALIDES; ALKYLBORONIC ESTERS; BORONIC ACID; ARYL; HYDROBORATION; ETHERS; DERIVATIVES;
D O I
10.1021/jo3021665
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.
引用
收藏
页码:10399 / 10408
页数:10
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