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

被引:64
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
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.
引用
收藏
页码:7581 / 7584
页数:4
相关论文
共 75 条
[1]   Regioselective C-H Activation of Substituted Pyridines and other Azines using Mg- and Zn-TMP-Bases [J].
Balkenhohl, Moritz ;
Knochel, Paul .
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 [J].
Balkenhohl, Moritz ;
Salgues, Bruno ;
Hirai, Takahiro ;
Karaghiosoff, Konstantin ;
Knochel, Paul .
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) [J].
Balkenhohl, Moritz ;
Greiner, Robert ;
Makarov, Ilya S. ;
Heinz, Benjamin ;
Karaghiosoff, Konstantin ;
Zipse, Hendrik ;
Knochel, Paul .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (53) :13046-13050
[4]   A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].
Bates, CG ;
Gujadhur, RK ;
Venkataraman, D .
ORGANIC LETTERS, 2002, 4 (16) :2803-2806
[5]   Cobalt-Catalyzed Esterification of Amides [J].
Bourne-Branchu, Yann ;
Gosmini, Corinne ;
Danoun, Gregory .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (42) :10043-10047
[6]   Selective functionalization of cyano-phenyl-2-oxazolines using TMPMgCl•LiCl [J].
Bozzini, Leandro A. ;
Batista, Joao H. C. ;
de Mello, Murilo B. M. ;
Vessecchi, Ricardo ;
Clososki, Giuliano C. .
TETRAHEDRON LETTERS, 2017, 58 (44) :4186-4190
[7]   Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C-S Coupling [J].
Bryan, Christopher S. ;
Braunger, Julia A. ;
Lautens, Mark .
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 [J].
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther ;
Tellitu, Imanol .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5100-5105
[9]   Zincation and Magnesiation of Functionalized Silylated Cyanohydrins Using TMP-Bases [J].
Castello-Mico, Alicia ;
Knochel, Paul .
SYNTHESIS-STUTTGART, 2018, 50 (01) :155-169
[10]   Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates [J].
Chen, Yi-Hung ;
Grassl, Simon ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (04) :1108-1111