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Rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp²)-H/alkene functionalization.
Angew Chem Int Ed Engl. 2014 Oct 13; 53(42):11338-41.AC

Abstract

This study describes a new rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp(2))-H bond and addition/protonolysis of an alkene C=C bond. This method is applicable to a wide range of 5-aryl-2,3-dihydro-1H-pyrroles and internal alkynes, and results in the assembly of the spiro[indene-1,2'-pyrrolidine] architectures in good yields with excellent regioselectivities.

Authors+Show Affiliations

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

25195874

Citation

Zhou, Ming-Bo, et al. "Rhodium(III)-catalyzed [3+2] Annulation of 5-aryl-2,3-dihydro-1H-pyrroles With Internal Alkynes Through C(sp²)-H/alkene Functionalization." Angewandte Chemie (International Ed. in English), vol. 53, no. 42, 2014, pp. 11338-41.
Zhou MB, Pi R, Hu M, et al. Rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp²)-H/alkene functionalization. Angew Chem Int Ed Engl. 2014;53(42):11338-41.
Zhou, M. B., Pi, R., Hu, M., Yang, Y., Song, R. J., Xia, Y., & Li, J. H. (2014). Rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp²)-H/alkene functionalization. Angewandte Chemie (International Ed. in English), 53(42), 11338-41. https://doi.org/10.1002/anie.201407175
Zhou MB, et al. Rhodium(III)-catalyzed [3+2] Annulation of 5-aryl-2,3-dihydro-1H-pyrroles With Internal Alkynes Through C(sp²)-H/alkene Functionalization. Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11338-41. PubMed PMID: 25195874.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp²)-H/alkene functionalization. AU - Zhou,Ming-Bo, AU - Pi,Rui, AU - Hu,Ming, AU - Yang,Yuan, AU - Song,Ren-Jie, AU - Xia,Yuanzhi, AU - Li,Jin-Heng, Y1 - 2014/09/04/ PY - 2014/07/14/received PY - 2014/9/9/entrez PY - 2014/9/10/pubmed PY - 2015/6/30/medline KW - alkynes KW - annulation KW - heterocycles KW - rhodium KW - spiro compounds SP - 11338 EP - 41 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 42 N2 - This study describes a new rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp(2))-H bond and addition/protonolysis of an alkene C=C bond. This method is applicable to a wide range of 5-aryl-2,3-dihydro-1H-pyrroles and internal alkynes, and results in the assembly of the spiro[indene-1,2'-pyrrolidine] architectures in good yields with excellent regioselectivities. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/25195874/Rhodium_III__catalyzed_[3+2]_annulation_of_5_aryl_23_dihydro_1H_pyrroles_with_internal_alkynes_through_C_sp��__H/alkene_functionalization_ L2 - https://doi.org/10.1002/anie.201407175 DB - PRIME DP - Unbound Medicine ER -