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Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization.
Angew Chem Int Ed Engl. 2015 May 26; 54(22):6595-9.AC

Abstract

A rhodium(III)-catalyzed [3+2]/[5+2] annulation of 4-aryl 1-tosyl-1,2,3-triazoles with internal alkynes is presented. This transformation provides straightforward access to indeno[1,7-cd]azepine architectures through a sequence involving the formation of a rhodium(III) azavinyl carbene, dual C(sp(2))-H functionalization, and [3+2]/[5+2] annulation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yang Y
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Zhou MB
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Ouyang XH
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Pi R
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Song RJ
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
Li JH
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China). jhli@hnu.edu.cn. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China). jhli@hnu.edu.cn.

MeSH

AlkynesAzepinesCarbonCatalysisCycloaddition ReactionHydrogenRhodiumTriazoles

Pub Type(s)

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

Language

eng

PubMed ID

25872912

Citation

Yang, Yuan, et al. "Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles With Internal Alkynes Through Dual C(sp2)-H Functionalization." Angewandte Chemie (International Ed. in English), vol. 54, no. 22, 2015, pp. 6595-9.
Yang Y, Zhou MB, Ouyang XH, et al. Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization. Angew Chem Int Ed Engl. 2015;54(22):6595-9.
Yang, Y., Zhou, M. B., Ouyang, X. H., Pi, R., Song, R. J., & Li, J. H. (2015). Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization. Angewandte Chemie (International Ed. in English), 54(22), 6595-9. https://doi.org/10.1002/anie.201501260
Yang Y, et al. Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles With Internal Alkynes Through Dual C(sp2)-H Functionalization. Angew Chem Int Ed Engl. 2015 May 26;54(22):6595-9. PubMed PMID: 25872912.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization. AU - Yang,Yuan, AU - Zhou,Ming-Bo, AU - Ouyang,Xuan-Hui, AU - Pi,Rui, AU - Song,Ren-Jie, AU - Li,Jin-Heng, Y1 - 2015/04/14/ PY - 2015/02/09/received PY - 2015/4/16/entrez PY - 2015/4/16/pubmed PY - 2016/2/26/medline KW - alkynes KW - annulation KW - indeno[1,7-cd]azepines KW - rhodium KW - triazoles SP - 6595 EP - 9 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 22 N2 - A rhodium(III)-catalyzed [3+2]/[5+2] annulation of 4-aryl 1-tosyl-1,2,3-triazoles with internal alkynes is presented. This transformation provides straightforward access to indeno[1,7-cd]azepine architectures through a sequence involving the formation of a rhodium(III) azavinyl carbene, dual C(sp(2))-H functionalization, and [3+2]/[5+2] annulation. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/25872912/Rhodium_III__Catalyzed_[3+2]/[5+2]_Annulation_of_4_Aryl_123_Triazoles_with_Internal_Alkynes_through_Dual_C_sp2__H_Functionalization_ DB - PRIME DP - Unbound Medicine ER -