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

页码：5578 / 5581

页数：4

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