Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and Aldehydes via Aryl-Aryl Amino Group Migration

被引：66
作者：
Bhojgude, Sachin Suresh [1 ]
Bayiskar, Dnyaneshwar R. [1 ]
Gonnade, Rajesh G. [2 ]
Biju, Akkattu T. [1 ]
机构：
[1] CSIR Natl Chem Lab, Organ Chem Div, Pune 411008, Maharashtra, India
[2] CSIR Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 24期
关键词：
TRANSITION-METAL-FREE; FACILE N-ARYLATION; TERMINAL ALKYNES; STRAIGHTFORWARD SYNTHESIS; MULTICOMPONENT REACTION; PRACTICAL SYNTHESIS; EMPLOYING ARYNES; ACCESS; BOND; BENZYNE;
D O I：
10.1021/acs.orglett.5b03319
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The transition-Metal-free multicomponent coupling of arynes, aromatic tertiary amines, and aldehydes proceeding via the aryl to aryl amino group migration has been demonstrated. This protocol allows rapid access to ortho-functionalized tertiary amines in moderate to good yields. Moreover, activated ketones can also be used as the aldehyde Component in the present reaction. The similarity of the aryl-aryl tertiary amino group migration with the Smiles rearrangement is striking.
引用
收藏
页码：6270 / 6273
页数：4
相关论文
共 58 条
[1]   Benzannulated Bicycles by Three-Component Aryne Reactions [J].
Allan, Kevin M. ;
Gilmore, Christopher D. ;
Stoltz, Brian M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (19) :4488-4491
[2]   Cycloaddition Reaction of 2-Vinylazetidines with Benzyne: A Facile Access to 1-Benzazocine Derivatives [J].
Aoki, Takashi ;
Koya, Shunsuke ;
Yamasaki, Ryu ;
Saito, Shinichi .
ORGANIC LETTERS, 2012, 14 (17) :4506-4509
[3]   Employing Arynes in Transition-Metal-Free Monoarylation of Aromatic Tertiary Amines [J].
Bhojgude, Sachin Suresh ;
Kaicharla, Trinadh ;
Biju, Akkattu T. .
ORGANIC LETTERS, 2013, 15 (21) :5452-5455
[4]   Arynes in Transition-Metal-Free Multicomponent Coupling Reactions [J].
Bhojgude, Sachin Suresh ;
Biju, Akkattu T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1520-1522
[5]   Rapid Access to Benzoxaphospholes and Their Spiro Analogues by a Three-Component Coupling Involving Arynes, Phosphines, and Activated Ketones [J].
Bhunia, Anup ;
Roy, Tony ;
Gonnade, Rajesh G. ;
Biju, Akkattu T. .
ORGANIC LETTERS, 2014, 16 (19) :5132-5135
[6]   Multicomponent reactions involving phosphines, arynes and aldehydes [J].
Bhunia, Anup ;
Kaicharla, Trinadh ;
Porwal, Digvijay ;
Gonnade, Rajesh G. ;
Biju, Akkattu T. .
CHEMICAL COMMUNICATIONS, 2014, 50 (77) :11389-11392
[7]   Employing Arynes in Transition-Metal-Free, N-Heterocycle- Initiated Multicomponent Reactions [J].
Bhunia, Anup ;
Biju, Akkattu T. .
SYNLETT, 2014, 25 (05) :608-614
[8]   Transition-Metal-Free Multicomponent Reactions Involving Arynes, N-Heterocycles, and Isatins [J].
Bhunia, Anup ;
Roy, Tony ;
Pachfule, Pradip ;
Rajamohanan, Pattuparambil R. ;
Biju, Akkattu T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :10040-10043
[9]   Multicomponent Reactions Involving Arynes, Quinolines, and Aldehydes [J].
Bhunia, Anup ;
Porwal, Digvijay ;
Gonnade, Rajesh G. ;
Biju, Akkattu T. .
ORGANIC LETTERS, 2013, 15 (17) :4620-4623
[10]   Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].
Bhunia, Anup ;
Yetra, Santhivardhana Reddy ;
Biju, Akkattu T. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152
123456