Metal and base free synthesis of primary amines via ipso amination of organoboronic acids mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA)

被引：22

作者：

Chatterjee, Nachiketa ^{[1
]}

Goswami, Avijit ^{[1
]}

机构：

[1] IIT Ropar, Dept Chem, Rupnagar 140001, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 29期

关键词：

BORONIC ACIDS; ALKYLBORONIC ACIDS/ESTERS; CATALYZED AMINATION; COUPLING REACTIONS; BOND FORMATION; C-N; ARYL; HYDROXYLATION; ANILINES; GUIDE;

D O I：

10.1039/c5ob01070e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal and base free synthesis of primary amines has been developed at ambient temperature through ipso amination of diversely functionalized organoboronic acids, employing a combination of [bis(trifluoroacetoxy)iodo]benzene (PIFA)-N-bromosuccinimide (NBS) and methoxyamine hydrochloride as the aminating reagent. The amines were primarily obtained as their trifluoroacetate salts which on subsequent aqueous alkaline work up provided the corresponding free amines. The combination of PIFA-NBS is found to be the mildest choice compared to the commonly used strong bases (e.g. n-BuLi, Cs2CO3) for activating the aminating agent. The reaction is expected to proceed via activation of the aminating reagent followed by B-N 1,2-aryl migration.

引用

页码：7940 / 7945

页数：6

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