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Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by alpha-aryldiazoesters.
Org Lett. 2010 Feb 05; 12(3):604-7.OL

Abstract

A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl(2)(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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Publisher Full Text (DOI)

Authors+Show Affiliations

Chan WW
Open Laboratory of Chirotechnology, The Institute of Molecular Technology for Drug Discovery and Synthesis and the Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
Yeung SH
No affiliation info available
Zhou Z
No affiliation info available
Chan AS
No affiliation info available
Yu WY
No affiliation info available

MeSH

CatalysisCombinatorial Chemistry TechniquesIndolesMolecular StructureRutheniumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20043644

Citation

Chan, Wai-Wing, et al. "Ruthenium Catalyzed Directing Group-free C2-selective Carbenoid Functionalization of Indoles By Alpha-aryldiazoesters." Organic Letters, vol. 12, no. 3, 2010, pp. 604-7.
Chan WW, Yeung SH, Zhou Z, et al. Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by alpha-aryldiazoesters. Org Lett. 2010;12(3):604-7.
Chan, W. W., Yeung, S. H., Zhou, Z., Chan, A. S., & Yu, W. Y. (2010). Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by alpha-aryldiazoesters. Organic Letters, 12(3), 604-7. https://doi.org/10.1021/ol9028226
Chan WW, et al. Ruthenium Catalyzed Directing Group-free C2-selective Carbenoid Functionalization of Indoles By Alpha-aryldiazoesters. Org Lett. 2010 Feb 5;12(3):604-7. PubMed PMID: 20043644.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by alpha-aryldiazoesters. AU - Chan,Wai-Wing, AU - Yeung,Shing-Hin, AU - Zhou,Zhongyuan, AU - Chan,Albert S C, AU - Yu,Wing-Yiu, PY - 2010/1/2/entrez PY - 2010/1/2/pubmed PY - 2010/3/6/medline SP - 604 EP - 7 JF - Organic letters JO - Org Lett VL - 12 IS - 3 N2 - A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl(2)(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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20043644/Ruthenium_catalyzed_directing_group_free_C2_selective_carbenoid_functionalization_of_indoles_by_alpha_aryldiazoesters_ L2 - https://doi.org/10.1021/ol9028226 DB - PRIME DP - Unbound Medicine ER -