Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents

被引：13
作者：
He, Yimiao [1 ]
Huang, Lilan [1 ]
Xie, Limei [1 ]
Liu, Peng [3 ]
Wei, Qiongmei [2 ]
Mao, Fangfang [1 ]
Zhang, Xuehong [1 ]
Huang, Jun [1 ]
Chen, Sijing [1 ]
Huang, Chusheng [1 ]
机构：
[1] Nanning Normal Univ, Coll Chem & Mat, Guangxi Key Lab Nat Polymer Chem & Phys, Nanning 530001, Peoples R China
[2] Nanning Normal Univ, Coll Tourism & Culture, Nanning 530001, Peoples R China
[3] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, 190 Kaiyuan Ave, Guangzhou 510530, Guangdong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 16期
基金：
中国国家自然科学基金;
关键词：
C(SP(3))-H BONDS; PROTECTING GROUP; SOLVENT-FREE; ACID; HYDROXYLATION; ALCOHOLS; DERIVATIVES; TOSYLATION; 8-METHYLQUINOLINES; ACYLOXYLATION;
D O I：
10.1021/acs.joc.9b01278
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and operationally simple approach for palladium-catalyzed C-H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp(3))-H bonds, along with the hydroxylation and arylation of aryl C(sp(2))-H bonds, are successfully realized under mild conditions and with excellent site-selectivity. The versatile C-OSO2R bond provides a platform for a wide array of subsequent diversification reactions.
引用
收藏
页码：10088 / 10101
页数：14
相关论文
共 74 条
  • [1] Iron(I) in Negishi Cross-Coupling Reactions
    Adams, Christopher J.
    Bedford, Robin B.
    Carter, Emma
    Gower, Nicholas J.
    Haddow, Mairi F.
    Harvey, Jeremy N.
    Huwe, Michael
    Angeles Cartes, M.
    Mansell, Stephen M.
    Mendoza, Carla
    Murphy, Damien M.
    Neeve, Emily C.
    Nunn, Joshua
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10333 - 10336
  • [2] Pentafluorophenyl sulfonate ester as a protecting group for the preparation of biaryl- and heterobiaryl sulfonate esters
    Avitabile, BG
    Smith, CA
    Judd, DB
    [J]. ORGANIC LETTERS, 2005, 7 (05) : 843 - 846
  • [3] Oxidative Cascade Reaction of N-Aryl-3-alkylideneazetidines and Carboxylic Acids: Access to Fused Pyridines
    Cai, Wangshui
    Wang, Shuang
    Jalani, Hitesh B.
    Wu, Junxian
    Lu, Hongjian
    Li, Guigen
    [J]. ORGANIC LETTERS, 2018, 20 (13) : 3833 - 3837
  • [4] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
  • [5] Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group
    Chen, Xiao-Yang
    Ozturk, Seyma
    Sorensen, Erik J.
    [J]. ORGANIC LETTERS, 2017, 19 (23) : 6280 - 6283
  • [6] Montmorillonite clay catalyzed tosylation of alcohols and selective monotosylation of diols with p-toluenesulfonic acid:: An enviro-economic route
    Choudary, BM
    Chowdari, NS
    Kantam, ML
    [J]. TETRAHEDRON, 2000, 56 (37) : 7291 - 7298
  • [7] Corbridge D. E. C., 2000, CHEM BIOCH TECHNOLOG
  • [8] ZrCl4 as an efficient catalyst for selective tosylation of alcohols with p-toluenesulfonic acid
    Das, B
    Reddy, VS
    [J]. CHEMISTRY LETTERS, 2004, 33 (11) : 1428 - 1429
  • [9] Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation
    Das, Prasenjit
    Saha, Debajyoti
    Saha, Dibyajyoti
    Guin, Joyram
    [J]. ACS CATALYSIS, 2016, 6 (09): : 6050 - 6054
  • [10] Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids
    DeBergh, J. Robb
    Niljianskul, Nootaree
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) : 10638 - 10641
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