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Issue 11, 2015
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Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates

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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.

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

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Publication details

The article was received on 29 Jun 2015, accepted on 17 Aug 2015 and first published on 19 Aug 2015


Article type: Edge Article
DOI: 10.1039/C5SC02343B
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Chem. Sci., 2015,6, 6654-6658
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    Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates

    Z. Chen, S. Liu, W. Hao, G. Xu, S. Wu, J. Miao, B. Jiang, S. Wang, S. Tu and G. Li, Chem. Sci., 2015, 6, 6654
    DOI: 10.1039/C5SC02343B

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