Ruthenium Catalyzed Directing Group-Free C2-Selective Carbenoid Functionalization of Indoles by α-Aryldiazoesters

被引:113
作者
Chan, Wai-Wing
Yeung, Shing-Hin
Zhou, Zhongyuan
Chan, Albert S. C.
Yu, Wing-Yiu [1 ]
机构
[1] Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China
关键词
C-H BOND; FRIEDEL-CRAFTS ALKYLATIONS; INTRAMOLECULAR CYCLOPROPANATION; ARYLATION; INSERTION; DECOMPOSITION; HETEROCYCLES; DIAZOESTERS; ACTIVATION; COMPLEXES;
D O I
10.1021/ol9028226
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)](2) as catalyst and alpha-aryldiazoesters as carbenoid source, 2-alkylated indoles were obtained in up to 96% isolated yield. Similarly, a regioselective carbenoid functionalization of NH-pyrroles was also achieved.
引用
收藏
页码:604 / 607
页数:4
相关论文
共 55 条
[1]   Selective tryptophan modification with rhodium carbenoids in aqueous solution [J].
Antos, JM ;
Francis, MB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10256-10257
[2]   A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].
Bandini, M ;
Melloni, A ;
Tommasi, S ;
Umani-Ronchi, A .
SYNLETT, 2005, (08) :1199-1222
[3]   Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Pesciaioli, Fabio ;
Sambri, Letizia ;
Melchiorre, Paolo .
ORGANIC LETTERS, 2007, 9 (07) :1403-1405
[4]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[5]   Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes [J].
Blay, Gonzalo ;
Fernandez, Isabel ;
Pedro, Jose R. ;
Vila, Carlos .
ORGANIC LETTERS, 2007, 9 (13) :2601-2604
[6]   Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].
Capito, E ;
Brown, JM ;
Ricci, A .
CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856
[7]   Asymmetric inter- and intramolecular cyclopropanation of alkenes catalyzed by chiral ruthenium porphyrins. Synthesis and crystal structure of a chiral metalloporphyrin carbene complex [J].
Che, CM ;
Huang, JS ;
Lee, FW ;
Li, Y ;
Lai, TS ;
Kwong, HL ;
Teng, PF ;
Lee, WS ;
Lo, WC ;
Peng, SM ;
Zhou, ZY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4119-4129
[8]   Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones [J].
Chen, Wei ;
Du, Wei ;
Yue, Lei ;
Li, Rui ;
Wu, Yong ;
Ding, Li-Sheng ;
Chen, Ying-Chun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) :816-821
[9]   Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles [J].
Cheung, WH ;
Zheng, SL ;
Yu, WY ;
Zhou, GC ;
Che, CM .
ORGANIC LETTERS, 2003, 5 (14) :2535-2538
[10]   Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides [J].
Choi, MKW ;
Yu, WY ;
Che, CM .
ORGANIC LETTERS, 2005, 7 (06) :1081-1084