Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions

被引：73
|
作者：
Zhu, Haibo [1 ,2 ]
Shen, Yajing [1 ]
Wen, Daheng [1 ]
Le, Zhang-Gao [2 ]
Tu, Tao [1 ,3 ]
机构：
[1] Fudan Univ, Shanghai Key Lab Mol Catalysis & Innovat Mat, Dept Chem, 2205 Songhu Rd, Shanghai 200438, Peoples R China
[2] East China Univ Technol, Sch Chem Biol & Mat Sci, Nanchang 330013, Jiangxi, Peoples R China
[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 04期
基金：
国家重点研发计划; 中国国家自然科学基金;
关键词：
ACENAPHTHOIMIDAZOLYLIDENE PALLADIUM COMPLEXES; SULFUR-DIOXIDE SURROGATE; CROSS-COUPLING REACTIONS; BORONIC ACIDS; DIARYLIODONIUM SALTS; GOLD CATALYSIS; ALKYL-HALIDES; ARYL; AMINATION; SULFONES;
D O I：
10.1021/acs.orglett.8b03957
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal -catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.
引用
收藏
页码：974 / 979
页数：6
相关论文
共 50 条
  • [1] Synthesis of ortho-substituted nitroaromatics via improved Negishi coupling conditions
    Tuttle, Jamison B.
    Azzarelli, Joseph M.
    Bechle, Bruce M.
    Dounay, Amy B.
    Evrard, Edelweiss
    Gan, Xinmin
    Ghosh, Somraj
    Henderson, Jaclyn
    Kim, Ji-Young
    Parikh, Vinod D.
    Verhoest, Patrick R.
    TETRAHEDRON LETTERS, 2011, 52 (41) : 5211 - 5213
  • [2] CONVERSIONS OF ORTHO-SUBSTITUTED NITROSOPHENYLCYCLOPROPANES, NITROPHENYLCYCLOPROPANES AND AZIDOPHENYLCYCLOPROPANES UNDER THE CONDITIONS OF NITRENE GENERATION
    MOCHALOV, SS
    FEDOTOV, AN
    SIZOV, AI
    SHABAROV, YS
    ZHURNAL ORGANICHESKOI KHIMII, 1979, 15 (07): : 1425 - 1431
  • [3] Synthesis of heterocycles via palladium-catalyzed carbonylation of ortho-substituted organic nitro compounds in relatively mild conditions
    Tollari, S., 1600, Publ by Elsevier Science Publishers B.V., Amsterdam, Netherlands (87): : 2 - 3
  • [4] SYNTHESIS OF HETEROCYCLES VIA PALLADIUM-CATALYZED CARBONYLATION OF ORTHO-SUBSTITUTED ORGANIC NITRO-COMPOUNDS IN RELATIVELY MILD CONDITIONS
    TOLLARI, S
    CENINI, S
    CROTTI, C
    GIANELLA, E
    JOURNAL OF MOLECULAR CATALYSIS, 1994, 87 (2-3): : 203 - 214
  • [5] MILD SELECTIVE HYDROLYSIS OF THE METHYL-ESTERS OF SOME ORTHO-SUBSTITUTED AROMATIC CARBOXYLIC-ACIDS
    COUTTS, IGC
    EDWARDS, M
    RICHARDS, DJ
    SYNTHESIS-STUTTGART, 1981, (06): : 487 - 489
  • [6] Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions
    Khodykina, Evgenia S.
    Steglenko, Dmitry V.
    Vetrova, Elena V.
    Pugachev, Artem D.
    Galkina, Maria S.
    Borodkina, Inna G.
    Lesin, Alexander V.
    Demidov, Oleg P.
    Metelitsa, Anatoly V.
    Kolodina, Alexandra A.
    CHEMISTRYSELECT, 2023, 8 (03):
  • [7] SYNTHESIS OF ORTHO-DEUTERATED PHENYLISOCYANATE UNDER MILD CONDITIONS
    MASSON, MA
    DORMOY, JR
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1979, 16 (05): : 785 - 789
  • [8] Selective synthesis of quinazolinones by using fluorescein catalyst under mild conditions
    Jin, Liang
    Chen, Xuehua
    Huang, Sheng
    Wang, Aixin
    Chen, Zhongsheng
    Le, Zhanggao
    Xie, Zongbo
    MOLECULAR CATALYSIS, 2023, 547
  • [9] Design, synthesis and biological evaluation of ortho-substituted phenethyl pyrazoles as selective glucocorticoid receptor modulators (SEGRMs)
    Perkins, James J.
    Bungard, Christopher
    Brandish, Philip
    Darimont, Beatrice
    Euler, Danielle
    Gambone, Carlo
    Hershey, James
    Leu, Chih-Tai
    Manikowski, Jesse J.
    McElwee-Witmer, Sheila
    McIntosh, Ian
    Schmidt, Azriel
    Thompson, Charles
    Vogel, Robert
    Meissner, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [10] Selective catalytic aerobic oxidation of substituted ethylbenzenes under mild conditions
    Melone, Lucio
    Prosperini, Simona
    Gambarotti, Cristian
    Pastori, Nadia
    Recupero, Francesco
    Punta, Carlo
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 355 : 155 - 160
12345