Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates

Zhen Zhen Chen, Shuai Liu, Wen Juan Hao, Ge Xu, Shuo Wu, Jiao Na Miao, Bo Jiang, Shu Liang Wang, Shu Jiang Tu, Guigen Li

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113 Scopus citations

Abstract

A catalytic bicyclization reaction of 1,5-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using TBAI (20 mol%) and Cu(OAc)2 (5 mol%) as co-catalysts under convenient conditions. In addition, the use of benzoyl peroxide (BPO) as the oxidant and pivalic acid (PivOH) as an additive was proven to be necessary for this reaction. The reactions occurred through 5-exo-dig/6-endo-trig bicyclizations and homolytic aromatic substitution (HAS) cascade mechanisms to give benzo[b]fluorens regioselectively. A similar catalytic process was developed for the synthesis of γ-ketosulfones. These reactions feature readily accessible starting materials and simple one-pot operation.

Original languageEnglish
Pages (from-to)6654-6658
Number of pages5
JournalChemical Science
Volume6
Issue number11
DOIs
StatePublished - Aug 19 2015

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