119th General Meeting of the KCS

Type Poster Presentation
Area 유기화학
Room No. 포스터발표장
Time 4월 20일 (목요일) 11:00~12:30
Code ORGN.P-227
Subject Synthesis of Benzofulvenes through Rhodium-Catalyzed Transannulation of Enynyl Triazoles
Authors 연의성, 변민현, 이필호*
강원대학교 화학과, Korea
Abstract

Benzofulvenes are key privileged scaffolds present in natural products, biologically and pharmacologically active molecules, functional materials, and metallocene catalysts. Due to its significance, it is still of considerable interest and necessity to develop efficient synthetic methods for functionalized benzofulvenes. Recently, N-sulfonyl-1,2,3-triazoles, easily obtained from click reactions, have been used for the preparation of a large number of heterocyclic and carbocyclic compounds through Rh-catalyzed denitrogenative cyclization. On the basis of these results, Rh-catalyzed denitrogenative cyclization of (E)-ethyl 2-(1-alkyl and arylsulfonyl-1H-1,2,3-triazol-4-yl)-3-aryl acrylate generated from (E)-ethyl 2-benzylidenebut-3-ynoates and N-sulfonyl azides in the presence of a copper catalyst was demonstrated for the synthesis of a wide range of functionalized benzofulvenes. Additionally, we have developed straightforward synthetic procedures for three benzofulvenes through tandem Cu-catalyzed [3 + 2] cycloaddition and Rh-catalyzed denitrogenative cyclization from (E)-ethyl 2-benzylidenebut-3-ynoates and N-sulfonyl azides in a one-pot.

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