Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement

被引：95
|
作者：
Holden, Catherine M. [1 ]
Sohel, Shariar M. A. [1 ]
Greaney, Michael F. [1 ]
机构：
[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 07期
基金：
英国工程与自然科学研究理事会;
关键词：
arynes; biaryls; heterocycles; rearrangements; synthetic methods; IPSO SUBSTITUTION; COUPLING REACTION; ARYNES SYNTHESIS; BIARYL COMPOUNDS; DIRECT ARYLATION; GENERATION; INSERTION; ROUTE; ACTIVATION; BIPHENYLS;
D O I：
10.1002/anie.201510236
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition- metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines.
引用
收藏
页码：2450 / 2453
页数：4
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