Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines

被引：103

作者：

Akram, Manjur O. ^{[1
,2
]}

Das, Avishek ^{[3
]}

Chakrabarty, Indradweep ^{[1
,2
]}

Patil, Nitin T. ^{[3
]}

机构：

[1] Natl Chem Lab, CSIR, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res, Ghaziabad 201002, India

[3] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

关键词：

VISIBLE-LIGHT PHOTOREDOX; C-H ACTIVATION; OXIDATIVE ADDITION; ACIDITIES; HALIDES; ALKYNYLATION; ANILINES; ALKYNES; COPPER; SALTS;

D O I：

10.1021/acs.orglett.9b03082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

引用

收藏

页码：8101 / 8105

页数：5

相关论文

共 52 条

[1] Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions [J].

Akram, Manjur O. ;

Banerjee, Somsuvra ;

Saswade, Sagar S. ;

Bedi, Vaibhav ;

Patil, Nitin T. .

CHEMICAL COMMUNICATIONS, 2018, 54 (79) :11069-11083

[2] Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis [J].

Akram, Manjur O. ;

Mali, Pramod S. ;

Patil, Nitin T. .

ORGANIC LETTERS, 2017, 19 (12) :3075-3078

[3]

[Anonymous], 2002, CROSS COUPLING REACT

[4] Gold-Catalyzed 1,2-Oxyalkynylation of N-Allenamides with Ethylnylbenziodoxolones [J].

Banerjee, Somsuvra ;

Senthilkumar, Beeran ;

Patil, Nitin T. .

ORGANIC LETTERS, 2019, 21 (01) :180-184

[5] Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)-C(sp) cross-coupling reactions [J].

Banerjee, Somsuvra ;

Patil, Nitin T. .

CHEMICAL COMMUNICATIONS, 2017, 53 (56) :7937-7940

[6] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[7] Electronic effects on the selectivity of Pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: The competitive roles of amine binding and acidity [J].

Biscoe, Mark R. ;

Barder, Timothy E. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) :7232-7235

[8] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[9] ACIDITIES OF ANILINES AND TOLUENES [J].

BORDWELL, FG ;

ALGRIM, D ;

VANIER, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1817-1819

[10] ACIDITIES OF ANILINES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG ;

ALGRIM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2964-2968

← 1 2 3 4 5 6 →