Radical-Enabled Bicyclization Cascades of Oxygen-Tethered 1,7-Enynes Leading to Skeletally Diverse Polycyclic Chromen-2-ones

Bo Jiang, Jie Li, Yuanyuan Pan, Wenjuan Hao, Guigen Li, Shujiang Tu

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Catalytic bicyclization cascades of oxygen-tethered 1,7-enynes with simple cycloalkanes or aryl sulfonhydrazides have been established via subsequent multiple C-C bond-forming events from alkynyl/alkenyl functions, delivering a series of densely functionalized tetracyclic chromen-2-ones in a functional-group-compatible manner. In the former, Fe-catalyzed spiro-bicyclization involves radical addition, 6-exo-dig cyclization, H-abstraction and 5-endo-trig cyclization sequences under mild conditions, resulting in new spiro-fused cyclopenta[c]chromen-2-ones via dual α,α-C(sp3)-H abstractions. The latter enables in-situ sulfonylation and desulfonylation of oxygen-tethered 1,7-enynes to realize the construction of multiple C-C bonds, thereby leading to the formation of naphtho[2,3-c]chromen-6-ones.

Original languageEnglish
Pages (from-to)323-334
Number of pages12
JournalChinese Journal of Chemistry
Volume35
Issue number3
DOIs
StatePublished - Mar 2017

Keywords

  • 1,7-enynes
  • C(sp)-H functionalization
  • bicyclization
  • fused chromen-2-ones
  • radical reaction

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