Metal-Free Photochemical C-Se Cross-Coupling of Aryl Halides with Diselenides

被引:15
|
作者
Wang, Ruizhe [1 ]
Wang, Xinyu [2 ]
Mao, Shuai [2 ]
Zhao, Yahao [2 ]
Yuan, Bo [2 ]
Yang, Xue-Yan [2 ]
Li, Jianjun [1 ]
Chen, Zhengkai [3 ]
机构
[1] Xi An Jiao Tong Univ, Sch Chem, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Xian 710049, Shaanxi, Peoples R China
[2] Xi An Jiao Tong Univ, Sch Pharm, Dept Med Chem, Xian 710061, Shaanxi, Peoples R China
[3] Zhejiang Sci Tech Univ, Dept Chem, Key Lab Surface & Interface Sci Polymer Mat Zheji, Hangzhou 310018, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
Aryl halides; Diselenides; Photochemistry; Radical reactions; C-Se bond coupling; DIARYL SELENIDES; DIPHENYL DISELENIDE; CATALYZED SYNTHESIS; CLEAVAGE; IODIDE; BORYLATION; DISULFIDE; CHEMISTRY; ANALOGS;
D O I
10.1002/adsc.202200042
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A light-mediated C-Se bond coupling reaction of aryl halides with diselenides under mild photocatalyst-free conditions for preparing aryl selenoethers has been achieved. The transformation is charactered by readily available materials, mild conditions, broad substrate scope and high efficiency. A reasonable mechanism has been proposed based on the preliminary mechanistic investigation. The protocol is also suitable for forging C-S bond and C-Te bond by the use of disulfides and ditellurides.
引用
收藏
页码:1607 / 1612
页数:6
相关论文
共 50 条
  • [41] Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides
    Everson, Daniel A.
    Weix, Daniel J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [42] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
    Everson, Daniel A.
    Shrestha, Ruja
    Weix, Daniel J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (03) : 920 - +
  • [43] C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols
    Maligres, Peter E.
    Li, Jing
    Krska, Shane W.
    Schreier, John D.
    Raheem, Izzat T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) : 9071 - 9074
  • [44] Indium-Catalyzed C-S Cross-Coupling of Aryl Halides with Thiols
    Reddy, V. Prakash
    Swapna, K.
    Kumar, A. Vijay
    Rao, K. Rama
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08): : 3189 - 3191
  • [45] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides
    Qian, Qun
    Zang, Zhenhua
    Wang, Shulin
    Chen, Yang
    Lin, Kunhua
    Gong, Hegui
    SYNLETT, 2013, 24 (05) : 619 - 624
  • [46] Enantioselective Cross-Coupling of meso-Epoxides with Aryl Halides
    Zhao, Yang
    Weix, Daniel J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) : 3237 - 3240
  • [47] Decarboxylative Cross-Coupling of Azoyl Carboxylic Acids with Aryl Halides
    Zhang, Fengzhi
    Greaney, Michael F.
    ORGANIC LETTERS, 2010, 12 (21) : 4745 - 4747
  • [48] Cobalt-Catalyzed Cross-Coupling Reactions Aryl Halides
    Gosmini, Corinne
    Moncomble, Aurelien
    ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) : 568 - 576
  • [49] Cross-coupling of alkynylsilanols with aryl halides promoted by potassium trimethylsilanolate
    Denmark, SE
    Tymonko, SA
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 9151 - 9154
  • [50] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
    ALHASSAN, MI
    SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420