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

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dc.creatorChen, Zhen Zhen
dc.creatorLiu, Shuai
dc.creatorHao, Wen Juan
dc.creatorXu, Ge
dc.creatorWu, Shuo
dc.creatorMiao, Jiao Na
dc.creatorJiang, Bo
dc.creatorWang, Shu Liang
dc.creatorTu, Shu Jiang
dc.creatorLi, Guigen (TTU)
dc.date.accessioned2023-04-10T20:39:13Z
dc.date.available2023-04-10T20:39:13Z
dc.date.issued2015
dc.description© The Royal Society of Chemistry. cc-by-nc
dc.description.abstractA 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.
dc.identifier.citationChen, Z.-Z., Liu, S., Hao, W.-J., Xu, G., Wu, S., Miao, J.-N., Jiang, B., Wang, S.-L., Tu, S.-J., & Li, G.. 2015. Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates. Chemical Science, 6(11). https://doi.org/10.1039/c5sc02343b
dc.identifier.urihttps://doi.org/10.1039/c5sc02343b
dc.identifier.urihttps://hdl.handle.net/2346/92698
dc.language.isoeng
dc.titleCatalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates
dc.typeArticle

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