共 55 条
Ruthenium Catalyzed Directing Group-Free C2-Selective Carbenoid Functionalization of Indoles by α-Aryldiazoesters
被引:113
作者:

Chan, Wai-Wing
论文数: 0 引用数: 0
h-index: 0
机构: Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China

Yeung, Shing-Hin
论文数: 0 引用数: 0
h-index: 0
机构: Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China

Zhou, Zhongyuan
论文数: 0 引用数: 0
h-index: 0
机构: Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China

Chan, Albert S. C.
论文数: 0 引用数: 0
h-index: 0
机构: Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China

Yu, Wing-Yiu
论文数: 0 引用数: 0
h-index: 0
机构:
Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China
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.
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页码:604 / 607
页数:4
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共 55 条
- [1] Selective tryptophan modification with rhodium carbenoids in aqueous solution[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) : 10256 - 10257Antos, JM论文数: 0 引用数: 0 h-index: 0机构: Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USAFrancis, MB论文数: 0 引用数: 0 h-index: 0机构: Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
- [2] A journey across recent advances in catalytic and stereoselective alkylation of indoles[J]. SYNLETT, 2005, (08) : 1199 - 1222Bandini, M论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, ItalyMelloni, A论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, ItalyTommasi, S论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, ItalyUmani-Ronchi, A论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
- [3] Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones[J]. ORGANIC LETTERS, 2007, 9 (07) : 1403 - 1405Bartoli, Giuseppe论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, ItalyBosco, Marcella论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, ItalyCarlone, Armando论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, ItalyPesciaioli, Fabio论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, ItalySambri, Letizia论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, ItalyMelchiorre, Paolo论文数: 0 引用数: 0 h-index: 0机构: Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy Univ Bologna, Alma Mater Studiorium, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
- [4] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents[J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365Beccalli, Egle M.论文数: 0 引用数: 0 h-index: 0机构: Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, Italy论文数: 引用数: h-index:机构:Martinelli, Michela论文数: 0 引用数: 0 h-index: 0机构: Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, ItalySottocornola, Silvia论文数: 0 引用数: 0 h-index: 0机构: Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, Italy
- [5] Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes[J]. ORGANIC LETTERS, 2007, 9 (13) : 2601 - 2604Blay, Gonzalo论文数: 0 引用数: 0 h-index: 0机构: Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, SpainFernandez, Isabel论文数: 0 引用数: 0 h-index: 0机构: Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, SpainPedro, Jose R.论文数: 0 引用数: 0 h-index: 0机构: Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, SpainVila, Carlos论文数: 0 引用数: 0 h-index: 0机构: Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Spain
- [6] Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles[J]. CHEMICAL COMMUNICATIONS, 2005, (14) : 1854 - 1856Capito, E论文数: 0 引用数: 0 h-index: 0机构: Chem Res Lab, Oxford OX1 3TA, EnglandBrown, JM论文数: 0 引用数: 0 h-index: 0机构: Chem Res Lab, Oxford OX1 3TA, EnglandRicci, A论文数: 0 引用数: 0 h-index: 0机构: Chem Res Lab, Oxford OX1 3TA, England
- [7] Asymmetric inter- and intramolecular cyclopropanation of alkenes catalyzed by chiral ruthenium porphyrins. Synthesis and crystal structure of a chiral metalloporphyrin carbene complex[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) : 4119 - 4129Che, CM论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaHuang, JS论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaLee, FW论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaLi, Y论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaLai, TS论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaKwong, HL论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaTeng, PF论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaLee, WS论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaLo, WC论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaPeng, SM论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R ChinaZhou, ZY论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
- [8] Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) : 816 - 821Chen, Wei论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R ChinaDu, Wei论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R ChinaYue, Lei论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R ChinaLi, Rui论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R ChinaWu, Yong论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R ChinaDing, Li-Sheng论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R ChinaChen, Ying-Chun论文数: 0 引用数: 0 h-index: 0机构: Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R China Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R China
- [9] Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles[J]. ORGANIC LETTERS, 2003, 5 (14) : 2535 - 2538Cheung, WH论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Peoples R ChinaZheng, SL论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Peoples R ChinaYu, WY论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Peoples R ChinaZhou, GC论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Peoples R ChinaChe, CM论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Peoples R China
- [10] Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides[J]. ORGANIC LETTERS, 2005, 7 (06) : 1081 - 1084Choi, MKW论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R ChinaYu, WY论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R ChinaChe, CM论文数: 0 引用数: 0 h-index: 0机构: Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synthesis, Hong Kong, Hong Kong, Peoples R China