One-Pot C-N/C-C Cross-Coupling of Methyliminodiacetic Acid Boronyl Arenes Enabled by Protective Enolization

被引：28
|
作者：
Grob, Jonathan E. [1 ]
Dechantsreiter, Michael A. [1 ]
Tichkule, Ritesh B. [1 ]
Connolly, Michael K. [1 ]
Honda, Ayako [1 ]
Tomlinson, Ronald C. [1 ]
Hamann, Lawrence G. [1 ]
机构：
[1] Novartis Inst BioMed Res Inc, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 21期
关键词：
MEDICINAL CHEMISTS; GENERAL STRATEGY; ARYL; TRIFLUOROMETHYLATION; ESTERS; COST;
D O I：
10.1021/ol302702q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Iterative cross-coupling is a highly efficient and versatile strategy for modular construction in organic synthesis, though this has historically been demonstrated solely in the context of C-C bond formation. A C-N cross-coupling of haloarene methyliminodiacetic acid (MIDA) boronates with a wide range of aromatic and aliphatic amines is reported. Successful cross-coupling of aliphatic amines was realized only through protective enolization of the MIDA group. This reaction paradigm was subsequently utilized to achieve a one-pot C-N/C-C cross-coupling sequence.
引用
收藏
页码：5578 / 5581
页数：4
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