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
相关论文
共 50 条
  • [1] A truce on the Smiles rearrangement: revisiting an old reaction-the Truce-Smiles rearrangement
    Snape, Timothy J.
    CHEMICAL SOCIETY REVIEWS, 2008, 37 (11) : 2452 - 2458
  • [2] α-Arylation of Aryl Ketones: Expanding the Scope of the Truce-Smiles Rearrangement
    Snape, Timothy J.
    SYNLETT, 2008, (17) : 2689 - 2691
  • [3] Photocatalytic Asymmetric Acyl Radical Truce-Smiles Rearrangement for the Synthesis of Enantioenriched α-Aryl Amides
    Ma, Wei-Yang
    Leone, Matteo
    Derat, Etienne
    Retailleau, Pascal
    Reddy, Chada Raji
    Neuville, Luc
    Masson, Geraldine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (37)
  • [4] A homologous enolate Truce-Smiles rearrangement
    Mitchell, LH
    Barvian, NC
    TETRAHEDRON LETTERS, 2004, 45 (29) : 5669 - 5671
  • [5] Truce-Smiles rearrangement of substituted phenyl ethers
    Kosowan, Joel R.
    W'Giorgis, Zemane
    Grewal, Ravneet
    Wood, Tabitha E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) : 6754 - 6765
  • [6] The Truce-Smiles rearrangement and related reactions: a review
    Henderson, Anna R. P.
    Kosowan, Joel R.
    Wood, Tabitha E.
    CANADIAN JOURNAL OF CHEMISTRY, 2017, 95 (05) : 483 - 504
  • [7] Truce-Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids
    Wang, Yu
    Pan, Wanying
    Zhang, Yuxuan
    Wang, Limin
    Han, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)
  • [8] EXAMPLE OF ALKYL GROUP TRANSFER IN A TRUCE-SMILES REARRANGEMENT
    SNYDER, DM
    TRUCE, WE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) : 5432 - 5433
  • [9] Aza-oxindole synthesis via base promoted Truce-Smiles rearrangement
    Dey, Chandan
    Katayev, Dmitry
    Ylijoki, Kai E. O.
    Kuendig, E. Peter
    CHEMICAL COMMUNICATIONS, 2012, 48 (89) : 10957 - 10959
  • [10] NHC-catalyzed Truce-Smiles rearrangement of N-aryl methacrylamides for the synthesis of trans-cinnamides
    Hu, Yuanyuan
    Wang, Zhen
    Luo, Honggen
    Jin, Hongwei
    Liu, Yunkui
    Zhou, Bingwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (17) : 3834 - 3837
12345