Ligand-Free Iridium-Catalyzed Borylation of Secondary Benzylic C-H Bonds

被引：5
作者：
Liu, Luhua [1 ,2 ]
Du, Rongrong [1 ,2 ]
Xu, Senmiao [1 ]
机构：
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 41卷 / 04期
基金：
中国国家自然科学基金;
关键词：
C-H activation; iridium; synthetic methods; borylation; DIRECTING GROUP; FUNCTIONALIZED ARENES; C(SP(3))-H BONDS; ACTIVATION; ARYLATION; RH; AMIDATION; COMPLEXES; PHENOLS; BETA;
D O I：
10.6023/cjoc202101009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The ligand-free regioselective iridium-catalyzed C(sp(3))-H bond borylation using pyrazole as the directing group is reported. The reaction occurs smoothly at the secondary benzylic position in the presence of a catalytic amount of commercially available [Ir(OMe)(cod)](2). A variety of functionalities could be well tolerated, affording corresponding products in good to excellent yields. The pyrazole could be degraded into amide by ozonolysis.
引用
收藏
页码：1572 / 1581
页数：10
相关论文
共 69 条
  • [1] Catalytic arylation reactions by C-H bond activation with aryl tosylates
    Ackermann, L
    Althammer, A
    Born, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2619 - 2622
  • [2] [RuCl3(H2O)n]-catalyzed direct arylations
    Ackermann, Lutz
    Althammer, Andreas
    Born, Robert
    [J]. TETRAHEDRON, 2008, 64 (26) : 6115 - 6124
  • [3] Hydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides
    Bai, Shao-Tao
    Bheeter, Charles B.
    Reek, Joost N. H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (37) : 13039 - 13043
  • [4] Silyl-directed, iridium-catalyzed ortho-borylation of arenes. A one-pot ortho-borylation of phenols, arylamines, and alkylarenes
    Boebel, Timothy A.
    Hartwig, John. F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) : 7534 - +
  • [5] Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade
    Boerth, Jeffrey A.
    Hummel, Joshua R.
    Ellman, Jonathan A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (41) : 12650 - 12654
  • [6] Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes
    Boller, TM
    Murphy, JM
    Hapke, M
    Ishiyama, T
    Miyaura, N
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14263 - 14278
  • [7] Bonet A, 2014, NAT CHEM, V6, P584, DOI [10.1038/NCHEM.1971, 10.1038/nchem.1971]
  • [8] Cu-catalyzed direct ortho-chlorination/-oxygenation of aryls: Switching of oxidant, control the diversity of products
    Botla, Vinayak
    Akudari, Ashok
    Malapaka, Chandrasekharam
    [J]. TETRAHEDRON LETTERS, 2019, 60 (02) : 115 - 119
  • [9] Rhodium(III)-Catalyzed Regioselective C-H Activation/Annulation for the Diverse Pyrazole-Core Substituted Furans
    Cai, Hongyun
    Thombal, Raju S.
    Li, Xin
    Lee, Yong Rok
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (17) : 4022 - 4032
  • [10] Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions
    Chattopadhyay, Buddhadeb
    Dannatt, Jonathan E.
    Andujar-De Sanctis, Ivonne L.
    Gore, Kristin A.
    Maleczka, Robert E., Jr.
    Singleton, Daniel A.
    Smith, Milton R., III
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) : 7864 - 7871
1234567