Palladium-catalyzed sp3 C-H activation of simple alkyl groups:: Direct preparation of indoline derivatives from N-alkyl-2-bromoanilines

被引:170
作者
Watanabe, Toshiaki [1 ]
Oishi, Shinya [1 ]
Fujii, Nobutaka [1 ]
Ohno, Hiroaki [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1021/ol800425z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The sp(3) C-H activation of a simple alkyl group catalyzed by palladium(0) provides a novel and convenient strategy for the synthesis of various indolines from simple precursors, such as N-alkyl-2-bromoanilines. This study demonstrates that assisting moieties in the substrate such as a pyridine or quaternary carbon are not always necessary for sp(3) C-H activation.
引用
收藏
页码:1759 / 1762
页数:4
相关论文
共 48 条
[1]   Mapping the kinase domain of Janus Kinase 3 [J].
Adams, C ;
Aldous, DJ ;
Amendola, S ;
Bamborough, P ;
Bright, C ;
Crowe, S ;
Eastwood, P ;
Fenton, G ;
Foster, M ;
Harrison, TKP ;
King, S ;
Lai, J ;
Lawrence, C ;
Letallec, JP ;
McCarthy, C ;
Moorcroft, N ;
Page, K ;
Rao, S ;
Redford, J ;
Sadiq, S ;
Smith, K ;
Souness, JE ;
Thurairatnam, S ;
Vine, M ;
Wyman, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (18) :3105-3110
[2]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[3]   The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups [J].
Baudoin, O ;
Herrbach, A ;
Guéritte, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5736-5740
[4]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[5]   Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].
Chatani, N ;
Asaumi, T ;
Yorimitsu, S ;
Ikeda, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941
[6]  
CHEN H, 2006, SCIENCE, V287, P14220
[7]   Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].
Chen, Xiao ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635
[8]   Organometallic alkane CH activation [J].
Crabtree, RH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4083-4091
[9]   Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates [J].
DeBoef, B ;
Pastine, SJ ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6556-6557
[10]   Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds [J].
Desai, LV ;
Hull, KL ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9542-9543