Alkylpotassium-Catalyzed Benzylic C-H Alkylation of Alkylarenes with Alkenes

被引:19
作者
Sato, Io [1 ]
Yamashita, Yasuhiro [1 ]
Kobayashi, Shu [1 ]
机构
[1] Univ Tokyo, Dept Chem, Sch Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
来源
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 01期
关键词
strong base; alkylarene; alkylation; alkylpotassium; alkene; POTASSIUM TERT-BUTOXIDE; 1,4-ADDITION REACTIONS; BOND ADDITION; BASE; ARYLATION; TOLUENE; DERIVATIVES; ACTIVATION; OLEFINS; LIGHT;
D O I
10.1055/s-0037-1610378
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic benzylic C-H alkylation reactions of alkylarenes with alkenes such as beta-substituted styrenes and vinylsilanes have been achieved by utilizing alkylpotassium as a catalyst. Various substituted toluene derivatives can be alkylated under mild reaction conditions to afford the desired functionalized hydrocarbons in moderate to high yields.
引用
收藏
页码:240 / 250
页数:11
相关论文
共 45 条
[1]   ACIDITIES OF ANILINES AND TOLUENES [J].
BORDWELL, FG ;
ALGRIM, D ;
VANIER, NR .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1817-1819
[2]   t-BuOK-Catalyzed addition of ketones and nitriles to vinylic silanes, phosphines and thio derivatives [J].
Bunlaksananusorn, T ;
Rodriguez, AL ;
Knochel, P .
CHEMICAL COMMUNICATIONS, 2001, (08) :745-746
[3]   Structurally Defined Potassium-Mediated Zincation of Pyridine and 4-R-Substituted Pyridines (R = Et, iPr, tBu, Ph, and Me2N) by Using Dialkyl-TMP-Zincate Bases [J].
Clegg, William ;
Conway, Ben ;
Graham, David V. ;
Hevia, Eva ;
Kennedy, Alan R. ;
Mulvey, Robert E. ;
Russo, Luca ;
Wright, Dominic S. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (29) :7074-7082
[4]   Chemoselective Activation of sp3 vs sp2 C-H Bonds with Pd(II) [J].
Curto, John M. ;
Kozlowski, Marisa C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) :18-21
[5]   Catalytic asymmetric benzylic C-H activation by means of carbenoid-induced C-H insertions [J].
Davies, HML ;
Jin, QH ;
Ren, PD ;
Kovalevsky, AY .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4165-4169
[6]   Applications of enantioselective carbolithiation of ortho-substituted β-methylstyrenes [J].
Hogan, Anne-Marie L. ;
Tricotet, Thomas ;
Meek, Alastair ;
Khokhar, Shaista S. ;
O'Shea, Donal F. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :6041-6044
[7]   Cooperation of a Nickel-Bipyridine Complex with Light for Benzylic C-H Arylation of Toluene Derivatives [J].
Ishida, Naoki ;
Masuda, Yusuke ;
Ishikawa, Norikazu ;
Murakami, Masahiro .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (06) :669-672
[8]  
Knochel P., 2014, COMPREHENSIVE ORGANI
[9]   Catalytic Carbanion Reactions: Formation and Reaction of Carbanions from Ester or Amide Equivalents Using Catalytic Amounts of Bases [J].
Kobayashi, Shu ;
Matsubara, Ryosuke .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) :10694-10700
[10]   Potassium-Zincate-Catalyzed Benzylic C-H Bond Addition of Diarylmethanes to Styrenes [J].
Liu, Yu-Feng ;
Zhai, Dan-Dan ;
Zhang, Xiang-Yu ;
Guan, Bing-Tao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (27) :8245-8249