Palladium-Catalyzed Chemoselective Borylation of (Poly)halogenated Aryl Triflates and Their Application in Consecutive Reactions

被引：11
|
作者：
Ng, Shan Shan [1 ,2 ]
Chen, Zicong [1 ,2 ]
Yuen, On Ying [1 ,2 ]
So, Chau Ming [1 ,2 ,3 ]
机构：
[1] Hong Kong Polytech Univ, State Key Lab Chem Biol & Drug Discovery, Hung Hom, Kowloon, Hong Kong, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hung Hom, Kowloon, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Shenzhen Res Inst, Shenzhen 518000, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 09期
基金：
中国国家自然科学基金;
关键词：
Palladium; Phosphines; Chemoselective reaction; Borylation; (Poly)halogenated aryl triflates; CROSS-COUPLING REACTION; HALIDES; SITE; REAGENTS; SYSTEM; LIGAND; ROUTE; MILD;
D O I：
10.1002/adsc.202101501
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
This study reports the palladium-catalyzed chemoselective borylation of (poly)halogenated aryl triflates with a reactivity order of C-Cl>C-OTf. A catalyst system comprising Pd(OAc)(2) and SelectPhos (L1) enables a reaction with high reactivity and chemoselectivity. The consecutively chemoselective borylation reaction followed by the chemoselective intermolecular Suzuki-Miyaura reaction can be performed using a one-pot two-step approach to synthesize unsymmetrical biaryl compounds containing the triflate moiety. The reaction can be scaled up to the gram scale without diminishing the yield and chemoselectivity.
引用
收藏
页码：1596 / 1601
页数：6
相关论文
共 50 条
  • [21] PALLADIUM-CATALYZED COUPLING REACTIONS OF (ALPHA-ETHOXYVINYL)TRIMETHYLSTANNANE WITH VINYL AND ARYL TRIFLATES
    KWON, HB
    MCKEE, BH
    STILLE, JK
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10): : 3114 - 3118
  • [22] A General Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Triflates
    Wu, Xiao-Feng
    Sundararaju, Basker
    Neumann, Helfried
    Dixneuf, Pierre H.
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) : 106 - 110
  • [23] A general palladium-catalyzed coupling of aryl bromides/triflates and thiols
    Itoh, T
    Mase, T
    ORGANIC LETTERS, 2004, 6 (24) : 4587 - 4590
  • [24] AN EFFICIENT PROCEDURE FOR PALLADIUM-CATALYZED REDUCTION OF ARYL/ENOL TRIFLATES
    KOTSUKI, H
    DATTA, PK
    HAYAKAWA, H
    SUENAGA, H
    SYNTHESIS-STUTTGART, 1995, (11): : 1348 - &
  • [25] Palladium-catalyzed reductive carbonylation of aryl triflates with synthesis gas
    Brenrifuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    SYNLETT, 2007, (16) : 2537 - 2540
  • [26] An Efficient Procedure for Palladium-Catalyzed Reduction of Aryl/Enol Triflates
    Kotsuki, H.
    Datta, P. K.
    Hayakawa, H.
    Suenaga, H.
    Synthesis, (11):
  • [27] An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates
    Wolfe, JP
    Ahman, J
    Sadighi, JP
    Singer, RA
    Buchwald, SL
    TETRAHEDRON LETTERS, 1997, 38 (36) : 6367 - 6370
  • [28] Palladium-Catalyzed Conversion of Aryl and Vinyl Triflates to Bromides and Chlorides
    Shen, Xiaoqiang
    Hyde, Alan M.
    Buchwald, Stephen L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) : 14076 - 14078
  • [29] An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates
    Tetrahedron Lett, 36 (6367):
  • [30] Ligand dearomatization and modification in the palladium-catalyzed fluorination of aryl triflates
    Milner, Phillip J.
    Buchwald, Stephen L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
12345