Homocoupling of Iodoarenes and Bromoalkanes Using Photoredox Gold Catalysis: A Light Enabled Au(III) Reductive Elimination

被引：36
作者：
Tran, Huy [1 ]
McCallum, Terry [1 ]
Morin, Mathieu [1 ]
Barriault, Louis [1 ]
机构：
[1] Univ Ottawa, Dept Chem & Biomol Sci, Ctr Catalysis Res & Innovat, Ottawa, ON, Canada
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 17期
基金：
加拿大自然科学与工程研究理事会;
关键词：
RADICAL CHEMISTRY; ALKYL-HALIDES; ORGANIC-DYES; REDOX; OXYARYLATION; DIMERIZATION; COMPLEXES; ELECTRON; FUNCTIONALIZATION; PHOTOCHEMISTRY;
D O I：
10.1021/acs.orglett.6b02021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The formation of homocoupled alkane byproducts have been identified in the reduction of bromoalkanes via photoredox gold catalysis with dimeric Au(I) complexes. This prompted further investigation into the mechanism of formation of these byproducts and the diversity of C-X bonds amenable to this transformation. Examples were found when considering bromoalkanes while a wide variety of iodoarenes underwent this process in good to excellent yields. The light enabled homocoupling of iodoarenes made possible by photoredox gold catalysis is reported.
引用
收藏
页码：4308 / 4311
页数：4
相关论文
共 88 条
  • [1] Green chemistry and photochemistry were born at the same time
    Albini, A
    Fagnoni, M
    [J]. GREEN CHEMISTRY, 2004, 6 (01) : 1 - 6
  • [2] Baguley PA, 1998, ANGEW CHEM INT EDIT, V37, P3073, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO
  • [3] 2-9
  • [4] Gold-Catalysed Oxyarylation of Styrenes and Mono- and gem-Disubstituted Olefins Facilitated by an Iodine(III) Oxidant
    Ball, Liam T.
    Lloyd-Jones, Guy C.
    Russell, Christopher A.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) : 2931 - 2937
  • [5] Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes
    Ball, Liam T.
    Green, Michael
    Lloyd-Jones, Guy C.
    Russell, Christopher A.
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 4724 - 4727
  • [6] Photochemical conversion of solar energy
    Balzani, Vincenzo
    Credi, Alberto
    Venturi, Margherita
    [J]. CHEMSUSCHEM, 2008, 1 (1-2) : 26 - 58
  • [7] Baudoin O., 2003, Studies in Natural Product Chemistry, V29, P355, DOI DOI 10.1016/S1572-5995(03)80011-X
  • [8] Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products
    Bringmann, Gerhard
    Gulder, Tanja
    Gulder, Tobias A. M.
    Breuning, Matthias
    [J]. CHEMICAL REVIEWS, 2011, 111 (02) : 563 - 639
  • [9] Palladium-Catalyzed, tert-Butyllithium-Mediated Dimerization of Aryl Halides and Its Application in the Atropselective Total Synthesis of Mastigophorene A
    Buter, Jeffrey
    Heijnen, Dorus
    Vila, Carlos
    Hornillos, Valentin
    Otten, Edwin
    Giannerini, Massimo
    Minnaard, Adriaan J.
    Feringa, Ben L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) : 3620 - 3624
  • [10] Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant
    Cai, Rong
    Lu, Mei
    Aguilera, Ellen Y.
    Xi, Yumeng
    Akhmedov, Novruz G.
    Petersen, Jeffrey L.
    Chen, Hao
    Shi, Xiaodong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8772 - 8776
123456789