Synthesis of Functionalized Diaryl Sulfides by Cobalt-Catalyzed Coupling between Arylzinc Pivalates and Diaryl Disulfides

被引：65
作者：
Dong, Zhi-Bing [1 ,2 ]
Balkenhohl, Moritz [2 ]
Tan, Eric [3 ]
Knochel, Paul [2 ]
机构：
[1] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Hubei, Peoples R China
[2] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany
[3] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 23期
基金：
中国国家自然科学基金;
关键词：
ENHANCED AIR; S-ARYLATION; (HETERO)ARYLZINC REAGENTS; ORGANIC SEMICONDUCTORS; NICKEL-CATALYST; CROSS-COUPLINGS; EFFICIENT; PALLADIUM; THIOLS; BOND;
D O I：
10.1021/acs.orglett.8b03319
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the cobalt-catalyzed preparation of diaryl sulfides from solid organozinc pivalates and commercially available diaryl disulfides is reported. This cross-coupling proceeds at room temperature and displays a good functional group tolerance, allowing the preparation of a diversity of symmetrical or asymmetrical diaryl sulfides in 60-95% yield.
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收藏
页码：7581 / 7584
页数：4
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    [J]. SYNOPEN, 2018, 2 (01): : 78 - 95
  • [2] Regioselective Metalation and Functionalization of the Pyrazolo[1,5-a]pyridine Scaffold Using Mg- and Zn-TMP Bases
    Balkenhohl, Moritz
    Salgues, Bruno
    Hirai, Takahiro
    Karaghiosoff, Konstantin
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2018, 20 (10) : 3114 - 3118
  • [3] Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl)
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    Greiner, Robert
    Makarov, Ilya S.
    Heinz, Benjamin
    Karaghiosoff, Konstantin
    Zipse, Hendrik
    Knochel, Paul
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (53) : 13046 - 13050
  • [4] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts
    Bates, CG
    Gujadhur, RK
    Venkataraman, D
    [J]. ORGANIC LETTERS, 2002, 4 (16) : 2803 - 2806
  • [5] Cobalt-Catalyzed Esterification of Amides
    Bourne-Branchu, Yann
    Gosmini, Corinne
    Danoun, Gregory
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (42) : 10043 - 10047
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    Bozzini, Leandro A.
    Batista, Joao H. C.
    de Mello, Murilo B. M.
    Vessecchi, Ricardo
    Clososki, Giuliano C.
    [J]. TETRAHEDRON LETTERS, 2017, 58 (44) : 4186 - 4190
  • [7] Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C-S Coupling
    Bryan, Christopher S.
    Braunger, Julia A.
    Lautens, Mark
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) : 7064 - 7068
  • [8] Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water
    Carril, Monica
    SanMartin, Raul
    Dominguez, Esther
    Tellitu, Imanol
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) : 5100 - 5105
  • [9] Zincation and Magnesiation of Functionalized Silylated Cyanohydrins Using TMP-Bases
    Castello-Mico, Alicia
    Knochel, Paul
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (01): : 155 - 169
  • [10] Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates
    Chen, Yi-Hung
    Grassl, Simon
    Knochel, Paul
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (04) : 1108 - 1111
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