"On Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

被引：55

作者：

Chakraborti, Gargi ^{[1
]}

Paladhi, Sushovan ^{[1
]}

Mandal, Tirtha ^{[1
]}

Dash, Jyotirmayee ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 14期

关键词：

CROSS-COUPLING REACTIONS; PALLADIUM-CATALYZED AMINATION; ARYL HALIDES; ALDOL REACTION; (HETERO)ARYL CHLORIDES; ORGANIC-SYNTHESIS; ROOM-TEMPERATURE; SECONDARY-AMINES; O-ARYLATION; COPPER;

D O I：

10.1021/acs.joc.7b03020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

引用

页码：7347 / 7359

页数：13

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