Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)-H Functionalization

Yuan Yang; Ming-Bo Zhou; Xuan-Hui Ouyang; Rui Pi; Ren-Jie Song; Jin-Heng Li

doi:10.1002/anie.201501260

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. doi: 10.1002/anie.201501260. Epub 2015 Apr 14.

Authors

Yuan Yang¹, Ming-Bo Zhou¹, Xuan-Hui Ouyang¹, Rui Pi¹, Ren-Jie Song¹, Jin-Heng Li^{2

3}

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China).
² State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China). jhli@hnu.edu.cn.
³ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China). jhli@hnu.edu.cn.

PMID: 25872912
DOI: 10.1002/anie.201501260

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.

Keywords: alkynes; annulation; indeno[1,7-cd]azepines; rhodium; triazoles.

Publication types

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

MeSH terms

Alkynes / chemistry*
Azepines / chemistry
Carbon / chemistry
Catalysis
Cycloaddition Reaction
Hydrogen / chemistry
Rhodium / chemistry*
Triazoles / chemistry*

Substances

Alkynes
Azepines
Triazoles
Carbon
Hydrogen
Rhodium