Meta-Selective C-H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether

被引:210
作者
Lee, Sunggi [1 ]
Lee, Hyelee [1 ]
Tan, Kian L. [1 ]
机构
[1] Boston Coll, Chestnut Hill, MA 02467 USA
关键词
IRIDIUM-CATALYZED BORYLATION; ELECTRON-DEFICIENT ARENES; BOND FORMATION; 1,3-DISUBSTITUTED ARENES; ORTHO-HALOGENATION; OLEFINATION; ACTIVATION; COMPLEXES; PALLADIUM; SILANOL;
D O I
10.1021/ja4107034
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A nitrile-based template that enables metaselective C-H bond functionalization was developed. The template is applicable to a range of substituted arenes and tolerates a variety of functional groups. The directing group uses a silicon atom for attachment, allowing for a facile introduction/deprotection strategy increasing the synthetic practicality of this template.
引用
收藏
页码:18778 / 18781
页数:4
相关论文
共 67 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] 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
  • [3] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
  • [4] Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation
    Boebel, Timothy A.
    Hartwig, John F.
    [J]. TETRAHEDRON, 2008, 64 (29) : 6824 - 6830
  • [5] Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation
    Chen, Bo
    Hou, Xue-Long
    Li, Yu-Xue
    Wu, Yun-Dong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7668 - 7671
  • [6] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
    Chen, Mark S.
    White, M. Christina
    [J]. SCIENCE, 2007, 318 (5851) : 783 - 787
  • [7] Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation
    Chen, Mark S.
    White, M. Christina
    [J]. SCIENCE, 2010, 327 (5965) : 566 - 571
  • [8] Chernyak N., 2010, J AM CHEM SOC, V132, P8270
  • [9] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds
    Cho, JY
    Tse, MK
    Holmes, D
    Maleczka, RE
    Smith, MR
    [J]. SCIENCE, 2002, 295 (5553) : 305 - 308
  • [10] Steric and chelate directing effects in aromatic borylation
    Cho, JY
    Iverson, CN
    Smith, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12868 - 12869