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Rhodium(III)-catalyzed direct selective C(5)-H oxidative annulations of 2-substituted imidazoles and alkynes by double C-H activation.
Org Lett. 2013 Apr 19; 15(8):1878-81.OL

Abstract

Double C-H activations of C(5)-H and Csp(2)-H of 2-substituted N-vinyl- or arylimidazoles were realized without heteroatom-directing assistance by rhodium(III) catalyst. A subsequent oxidative annulation reaction with alkynes efficiently produced aza-fused heterocycles with high molecular complexity in low to excellent yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Huang JR
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Zhang QR
No affiliation info available
Qu CH
No affiliation info available
Sun XH
No affiliation info available
Dong L
No affiliation info available
Chen YC
No affiliation info available

MeSH

AlkynesCatalysisCyclizationHeterocyclic CompoundsImidazolesMolecular StructureOxidation-ReductionRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23537406

Citation

Huang, Ji-Rong, et al. "Rhodium(III)-catalyzed Direct Selective C(5)-H Oxidative Annulations of 2-substituted Imidazoles and Alkynes By Double C-H Activation." Organic Letters, vol. 15, no. 8, 2013, pp. 1878-81.
Huang JR, Zhang QR, Qu CH, et al. Rhodium(III)-catalyzed direct selective C(5)-H oxidative annulations of 2-substituted imidazoles and alkynes by double C-H activation. Org Lett. 2013;15(8):1878-81.
Huang, J. R., Zhang, Q. R., Qu, C. H., Sun, X. H., Dong, L., & Chen, Y. C. (2013). Rhodium(III)-catalyzed direct selective C(5)-H oxidative annulations of 2-substituted imidazoles and alkynes by double C-H activation. Organic Letters, 15(8), 1878-81. https://doi.org/10.1021/ol400537b
Huang JR, et al. Rhodium(III)-catalyzed Direct Selective C(5)-H Oxidative Annulations of 2-substituted Imidazoles and Alkynes By Double C-H Activation. Org Lett. 2013 Apr 19;15(8):1878-81. PubMed PMID: 23537406.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(III)-catalyzed direct selective C(5)-H oxidative annulations of 2-substituted imidazoles and alkynes by double C-H activation. AU - Huang,Ji-Rong, AU - Zhang,Qian-Ru, AU - Qu,Chuan-Hua, AU - Sun,Xun-Hao, AU - Dong,Lin, AU - Chen,Ying-Chun, Y1 - 2013/03/28/ PY - 2013/3/30/entrez PY - 2013/3/30/pubmed PY - 2013/8/31/medline SP - 1878 EP - 81 JF - Organic letters JO - Org Lett VL - 15 IS - 8 N2 - Double C-H activations of C(5)-H and Csp(2)-H of 2-substituted N-vinyl- or arylimidazoles were realized without heteroatom-directing assistance by rhodium(III) catalyst. A subsequent oxidative annulation reaction with alkynes efficiently produced aza-fused heterocycles with high molecular complexity in low to excellent yields. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23537406/Rhodium_III__catalyzed_direct_selective_C_5__H_oxidative_annulations_of_2_substituted_imidazoles_and_alkynes_by_double_C_H_activation_ L2 - https://doi.org/10.1021/ol400537b DB - PRIME DP - Unbound Medicine ER -