Diamination of Domino Aryne Precursor with Sulfonamides

被引:58
作者
Qiu, Dachuan [1 ]
He, Jia [1 ]
Yue, Xiao [1 ]
Shi, Jiarong [1 ]
Li, Yang [1 ]
机构
[1] Chongqing Univ, Sch Chem & Chem Engn, 174 Shazheng St, Chongqing 400030, Peoples R China
关键词
THIA-FRIES REARRANGEMENT; FACILE N-ARYLATION; SYNTHETIC APPLICATIONS; ORGANIC-SYNTHESIS; BOND FORMATION; CHEMISTRY; BENZYNE; AMINES; CARBON; AMINOSILANES;
D O I
10.1021/acs.orglett.6b01334
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of a domino aryne precursor with sulfonamides efficiently afforded both 1,3-diaminobenzenes and trisubstituted 1,3-diaminobenzenes by simply varying the reaction conditions. Mechanistic study supports the sequential formation of two transient aryne intermediates involved in-the reaction.
引用
收藏
页码:3130 / 3133
页数:4
相关论文
共 38 条
[1]   Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides [J].
Beller, M ;
Breindl, C ;
Riermeier, TH ;
Tillack, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1403-1412
[2]   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
[3]   Indolynes as Electrophilic Indole Surrogates: Fundamental Reactivity and Synthetic Applications [J].
Bronner, Sarah M. ;
Bahnck, Kevin B. ;
Garg, Neil K. .
ORGANIC LETTERS, 2009, 11 (04) :1007-1010
[4]   The anionic thia-Fries rearrangement of aryl triflates [J].
Charmant, JPH ;
Dyke, AM ;
Lloyd-Jones, GC .
CHEMICAL COMMUNICATIONS, 2003, (03) :380-381
[5]   Indolyne and Aryne Distortions and Nucleophilic Regioselectivites [J].
Cheong, Paul H. -Y. ;
Paton, Robert S. ;
Bronner, Sarah M. ;
Im, G-Yoon J. ;
Garg, Neil K. ;
Houk, K. N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1267-+
[6]   Use of benzynes for the synthesis of heterocycles [J].
Dubrovskiy, Anton V. ;
Markina, Nataliya A. ;
Larock, Richard C. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (02) :191-218
[7]   Decoupling deprotonation from metalation:: Thia-Fries rearrangement [J].
Dyke, Alan M. ;
Gill, Duncan M. ;
Harvey, Jeremy N. ;
Hester, Alison J. ;
Lloyd-Jones, Guy C. ;
Munoz, M. Paz ;
Shepperson, Ian R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5067-5070
[8]   Arynes and Cyclohexyne in Natural Product Synthesis [J].
Gampe, Christian M. ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) :3766-3778
[9]   Double Heteroatom Functionalization of Arenes Using Benzyne Three-Component Coupling [J].
Garcia-Lopez, Jose-Antonio ;
Cetin, Meliha ;
Greaney, Michael F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (07) :2156-2159
[10]   Pyridynes and indolynes as building blocks for functionalized heterocycles and natural products [J].
Goetz, Adam E. ;
Shah, Tejas K. ;
Garg, Neil K. .
CHEMICAL COMMUNICATIONS, 2015, 51 (01) :34-45