Pd-Catalyzed Site-SelectiveBorylation of Simple Arenes via Thianthrenation

被引:31
作者
Chen, Xiao-Yue [1 ,2 ]
Huang, Yu-Hao [2 ]
Zhou, Jian [1 ]
Wang, Peng [2 ,3 ]
机构
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, 3663N Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organometall Chem, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[3] Chinese Acad Sci, CAS Key Lab Energy Regulat Mat, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Borylation; Arene; Site-selective; Palladium; Sulfonium salts; C-H FUNCTIONALIZATION; PARA-SELECTIVE ARYLATION; BOND FORMATION; BORYLATION; ACIDS; SUBSTITUTION; AMINATION; SALTS;
D O I
10.1002/cjoc.202000212
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
of main observation and conclusion Site-selective borylation of simple arenes was realized in one potviaan electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.
引用
收藏
页码:1269 / 1272
页数:4
相关论文
共 54 条
  • [1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [2] Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation
    Aukland, Miles H.
    Siauciulis, Mindaugas
    West, Adam
    Perry, Gregory J. P.
    Procter, David J.
    [J]. NATURE CATALYSIS, 2020, 3 (02) : 163 - 169
  • [3] An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence
    Aukland, Miles H.
    Talbot, Fabien J. T.
    Fernandez-Salas, Jose A.
    Ball, Matthew
    Pulis, Alexander P.
    Procter, David J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (31) : 9785 - 9789
  • [4] Site-selective and versatile aromatic C-H functionalization by thianthrenation
    Berger, Florian
    Plutschack, Matthew B.
    Riegger, Julian
    Yu, Wanwan
    Speicher, Samira
    Ho, Matthew
    Frank, Nils
    Ritter, Tobias
    [J]. NATURE, 2019, 567 (7747) : 223 - 228
  • [5] Boursalian GB, 2016, NAT CHEM, V8, P810, DOI [10.1038/NCHEM.2529, 10.1038/nchem.2529]
  • [6] Dual Ligand-Enabled Nondirected C-H Olefination of Arenes
    Chen, Hao
    Wedi, Philipp
    Meyer, Tim
    Tavakoli, Ghazal
    van Gemmeren, Manuel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2497 - 2501
  • [7] Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles
    Chen, Junting
    Li, Jiakun
    Plutschack, Matthew B.
    Berger, Florian
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5616 - 5620
  • [8] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
  • [9] para-Selective arylation and alkenylation of monosubstituted arenes using thianthrene S-oxide as a transient mediator
    Chen, Xiao-Yue
    Nie, Xiao-Xue
    Wu, Yichen
    Wang, Peng
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (37) : 5058 - 5061
  • [10] Synthesis of β-Arylethenesulfonyl Fluoride via Pd-Catalyzed Nondirected C-H Alkenylation
    Chen, Xiao-Yue
    Wu, Yichen
    Zhou, Jian
    Wang, Peng
    Yu, Jin-Quan
    [J]. ORGANIC LETTERS, 2019, 21 (05) : 1426 - 1429