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Rhodium/copper-catalyzed annulation of benzimides with internal alkynes: indenone synthesis through sequential C-H and C-N cleavage.
Angew Chem Int Ed Engl. 2012 Apr 16; 51(16):3948-52.AC

Abstract

Doubled up: a rhodium(III)/copper(II) system co-catalyzes the annulation of benzimides with internal alkynes for the synthesis of indenones (see scheme; Cp*=C(5) Me(5)). The reaction involves an uncommon nucleophilic addition of a transition-metal-carbon bond to an imide moiety. This novel reaction provides a facile route to synthesize indenones from readily available benzimides and internal alkynes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li BJ
Beijing National Laboratory of Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, China.
Wang HY
No affiliation info available
Zhu QL
No affiliation info available
Shi ZJ
No affiliation info available

MeSH

AlkynesCarbonCatalysisCopperCyclizationHydrogenImidesNitrogenRhodium

Pub Type(s)

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

Language

eng

PubMed ID

22396146

Citation

Li, Bi-Jie, et al. "Rhodium/copper-catalyzed Annulation of Benzimides With Internal Alkynes: Indenone Synthesis Through Sequential C-H and C-N Cleavage." Angewandte Chemie (International Ed. in English), vol. 51, no. 16, 2012, pp. 3948-52.
Li BJ, Wang HY, Zhu QL, et al. Rhodium/copper-catalyzed annulation of benzimides with internal alkynes: indenone synthesis through sequential C-H and C-N cleavage. Angew Chem Int Ed Engl. 2012;51(16):3948-52.
Li, B. J., Wang, H. Y., Zhu, Q. L., & Shi, Z. J. (2012). Rhodium/copper-catalyzed annulation of benzimides with internal alkynes: indenone synthesis through sequential C-H and C-N cleavage. Angewandte Chemie (International Ed. in English), 51(16), 3948-52. https://doi.org/10.1002/anie.201200271
Li BJ, et al. Rhodium/copper-catalyzed Annulation of Benzimides With Internal Alkynes: Indenone Synthesis Through Sequential C-H and C-N Cleavage. Angew Chem Int Ed Engl. 2012 Apr 16;51(16):3948-52. PubMed PMID: 22396146.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium/copper-catalyzed annulation of benzimides with internal alkynes: indenone synthesis through sequential C-H and C-N cleavage. AU - Li,Bi-Jie, AU - Wang,Hao-Yuan, AU - Zhu,Qi-Lei, AU - Shi,Zhang-Jie, Y1 - 2012/03/06/ PY - 2012/01/11/received PY - 2012/3/8/entrez PY - 2012/3/8/pubmed PY - 2012/8/2/medline SP - 3948 EP - 52 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 51 IS - 16 N2 - Doubled up: a rhodium(III)/copper(II) system co-catalyzes the annulation of benzimides with internal alkynes for the synthesis of indenones (see scheme; Cp*=C(5) Me(5)). The reaction involves an uncommon nucleophilic addition of a transition-metal-carbon bond to an imide moiety. This novel reaction provides a facile route to synthesize indenones from readily available benzimides and internal alkynes. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/22396146/Rhodium/copper_catalyzed_annulation_of_benzimides_with_internal_alkynes:_indenone_synthesis_through_sequential_C_H_and_C_N_cleavage_ L2 - https://doi.org/10.1002/anie.201200271 DB - PRIME DP - Unbound Medicine ER -