Tris(pentafluorophenyl)borane-Catalyzed Stereospecific Bromocyanation of Styrene Derivatives with Cyanogen Bromide

被引：2
|
作者：
Kiyokawa, Kensuke [1 ]
Noguchi, Ikumi [1 ]
Nagata, Takaya [1 ]
Minakata, Satoshi [1 ]
机构：
[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 14期
关键词：
NICKEL-CATALYZED CARBOCYANATION; INTRAMOLECULAR AMINOCYANATION; ELECTROPHILIC CYANATION; C-C; ALKENES; CYANIDE; PALLADIUM; ACTIVATION; INTERCONVERSION; HYDROCYANATION;
D O I：
10.1021/acs.orglett.3c00727
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We, herein, report on the bromocyanation of styrene derivatives with cyanogen bromide in the presence of tris(pentafluorophenyl)borane which functions as a Lewis acid catalyst that can effectively activate cyanogen bromide. This reaction proceeds through a stereospecific syn-addition. The protocol is operationally simple and provides practical access to beta-bromonitriles.
引用
收藏
页码：2537 / 2542
页数：6
相关论文
共 43 条
  • [31] Synthesis of Highly Branched Alkoxsiloxane-Dimethylsiloxane Copolymers by Nonhydrolytic Dehydrocarbon Polycondensation Catalyzed by Tris(pentafluorophenyl)borane
    Chojnowski, Julian
    Rubinsztajn, Slawomir
    Fortuniak, Witold
    Kurjata, Jan
    MACROMOLECULES, 2008, 41 (20) : 7352 - 7358
  • [32] Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition
    Prajapti, Santosh Kumar
    Nagarsenkar, Atulya
    Babu, Bathini Nagendra
    TETRAHEDRON LETTERS, 2014, 55 (10) : 1784 - 1787
  • [33] Coordination of Tetracyanoquinodimethane-Derivatives with Tris(pentafluorophenyl)borane Provides Stronger p-Dopants with Enhanced Stability
    Mansour, Ahmed E.
    Warren, Ross
    Lungwitz, Dominique
    Forster, Michael
    Scherf, Ullrich
    Opitz, Andreas
    Malischewski, Moritz
    Koch, Norbert
    ACS APPLIED MATERIALS & INTERFACES, 2023, 15 (39) : 46148 - 46156
  • [34] Reactions of titanium and zirconium derivatives of bis(trimethylsilyl)acetylene with tris(pentafluorophenyl)borane: A titanium(III) complex of an alkynylboranate
    Arndt, P
    Baumann, W
    Spannenberg, A
    Rosenthal, U
    Burlakov, VV
    Shur, VB
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) : 1414 - 1418
  • [35] SYNTHESIS AND PROPERTIES OF PENTAFLUOROPHENYLGALLIUM DERIVATIVES - THE PREPARATION OF TRIS(PENTAFLUOROPHENYL)GALLIUM AND ITS ADDUCTS, AND OF BIS(PENTAFLUOROPHENYL)GALLIUM BROMIDE, PENTAFLUOROPHENYLGALLIUM DIBROMIDE, AND TETRABUTYLAMMONIUM TETRAKIS(PENTAFLUOROPHENYL)GALLATE
    LUDOVICI, K
    TYRRA, W
    NAUMANN, D
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 441 (03) : 363 - 371
  • [36] Syndiospecific living polymerization of 4-methylstyrene and styrene with (trimethyl)pentamethylcyclopentadienyl-titanium/tris(pentafluorophenyl)borane/trioctylaluminum catalytic system
    Kawabe, M
    Murata, M
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2001, 39 (21) : 3692 - 3706
  • [37] Enantio- and Diastereoselective Carbonyl-Ene Cyclization-Acetalization Tandem Reaction Catalyzed by Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acids
    Ishihara, Hideyuki
    Huang, Jianhao
    Mochizuki, Takuya
    Hatano, Manabu
    Ishihara, Kazuaki
    ACS CATALYSIS, 2021, 11 (10) : 6121 - 6127
  • [38] Reaction of Bis(alkynyl)silanes with Tris(pentafluorophenyl)borane: Synthesis of Bulky Silole Derivatives by Means of 1,1-Carboboration under Mild Reaction Conditions
    Dierker, Gereon
    Ugolotti, Juri
    Kehr, Gerald
    Froehlich, Roland
    Erker, Gerhard
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) : 1080 - 1088
  • [39] Mechanism of Regioselective Ring-Opening Reactions of 1,2-Epoxyoctane Catalyzed by Tris(pentafluorophenyl)borane: A Combined Experimental, Density Functional Theory, and Microkinetic Study
    Yu, Ying
    Zhu, Youlong
    Bhagat, Mihir N.
    Raghuraman, Arjun
    Hirsekorn, Kurt F.
    Notestein, Justin M.
    Nguyen, SonBinh T.
    Broadbelt, Linda J.
    ACS CATALYSIS, 2018, 8 (12): : 11119 - 11133
  • [40] Tris(pentafluorophenyl)borane [B(C6F5)3]-catalyzed Friedel-Crafts reactions of activated arenes and heteroarenes with α-amidosulfones: the synthesis of unsymmetrical triarylmethanes
    Thirupathi, Ponnaboina
    Neupane, Lok Nath
    Lee, Keun-Hyeung
    TETRAHEDRON, 2011, 67 (38) : 7301 - 7310
12345