Synthesis of Fluorenes via Tandem Copper-Catalyzed [3+2] Cycloaddition and Rhodium-Catalyzed Denitrogenative Cyclization in a 5-Exo Mode from 2-Ethynylbiaryls and N-Sulfonyl Azides in One Pot

  • Seo, Boram
  • Jeon, Woo Hyung
  • Kim, Jaeeun
  • Kim, Sunghwa
  • Lee, Phil Ho
Citations

WEB OF SCIENCE

59
Citations

SCOPUS

62

초록

An efficient synthetic method of fluorenes having an enamine moiety at C-9 methylene bridge is developed from N-sulfonyl-4-biaryl-1,2,3-triazole derivatives via Rh-catalyzed denitrogenative cyclization in a 5-exo mode. Rh-catalyzed denitrogenative cyclization followed by catalytic hydrogenation produces N-tosylaminomethyl-substituted fluorenes in one pot. Moreover, fluorenes are synthesized via tandem Cu-catalyzed [3 + 2] cycloaddition and Rh-catalyzed denitrogenative cyclization in a 5-exo mode starting from 2-ethynylbiaryls and N-sulfonyl azides in one pot.

키워드

TERMINAL ALKYNESINTRAMOLECULAR ANNULATIONCONTROLLING SELECTIVITYORGANIC ELECTRONICSAROMATIC RINGSDERIVATIVESTRANSANNULATIONPYRROLES1,2,3-TRIAZOLES1-SULFONYL-1,2,3-TRIAZOLES
제목
Synthesis of Fluorenes via Tandem Copper-Catalyzed [3+2] Cycloaddition and Rhodium-Catalyzed Denitrogenative Cyclization in a 5-Exo Mode from 2-Ethynylbiaryls and N-Sulfonyl Azides in One Pot
저자
Seo, BoramJeon, Woo HyungKim, JaeeunKim, SunghwaLee, Phil Ho
DOI
10.1021/jo5027113
발행일
2015-01-16
유형
Article
저널명
The Journal of Organic Chemistry
80
2
페이지
722 ~ 732