Copper-Catalyzed N-Arylation of Tautomerizable Heterocycles with Boronic Acids and Its Application to Synthesis of Oxygenated Carbazoles

被引：32

作者：

Kumar, Karampoori Anil ^{[1
,2
]}

Kannaboina, Prakash ^{[1
,2
]}

Jaladanki, Chaitanya K. ^{[3
]}

Bharatam, Prasad V. ^{[3
]}

Das, Parthasarathi ^{[1
,2
]}

机构：

[1] AcSIR, Jammu-Campu,Canai Rd, Jammu 180001, India

[2] Indian Integrat Med CSIR, Div Med Chem, Canal Rd, Jammu 180001, India

[3] NIPER, Dept Med Chem, Sect 67, SAS Nagar 160012, Punjab, India

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 03期

关键词：

copper; N-arylation; tautomerizable heterocycle; boronic acids; oxygenated carbazoles; CROSS-COUPLING REACTIONS; C-N; NATURAL CARBAZOLES; ARYLBORONIC ACIDS; BISCARBAZOLE ALKALOIDS; BOND FORMATION; O-ARYLATION; H INSERTION; ARYL; EFFICIENT;

D O I：

10.1002/slct.201600147

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and mild strategy has been developed for the selective N-arylation of tautomerizable heterocycles with a series of arylboronic acids, using CuOTf as the catalyst and 1,10-Phen as the ligand, under base free conditions at ambient atmosphere. The reaction mechanism explored by using density functional methods revealed that both kinetic and thermodynamic controls favour N-arylation. This "open-flask" chemistry successfully applied for N-arylation of benzo[d] oxazol-2(3H)-one and the designed N-arylated product was subsequently manipulated in synthesizing various naturally occurring oxygenated carbazole alkaloids (e.g. clausenine, clauraila A, clausenal).

引用

页码：601 / 607

页数：7

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