title: Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates.
abstract: A catalytic bicyclization reaction of 1,5-enynes anchored by α,β-conjugates with arylsulfonyl radicals generatedin situfrom 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.
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Zhen-Zhen
authors.initials: ZZ
authors.lastname: Chen
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Shuai
authors.initials: S
authors.lastname: Liu
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Wen-Juan
authors.initials: WJ
authors.lastname: Hao
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Ge
authors.initials: G
authors.lastname: Xu
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Shuo
authors.initials: S
authors.lastname: Wu
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Jiao-Na
authors.initials: JN
authors.lastname: Miao
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Shu-Liang
authors.initials: SL
authors.lastname: Wang
authors.affiliation: Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials , Jiangsu Normal University , Xuzhou , 211116 , P. R. China . Email: jiangchem@jsnu.edu.cn ; Email: laotu@jsnu.edu.cn ; ; Tel: +8651683500065.
authors.forename: Shu-Jiang
authors.initials: SJ
authors.lastname: Tu
authors.affiliation: Institute of Chemistry & BioMedical Sciences , Collaborative Innovation Center of Chemistry for Life Sciences , School of Chem. and Chem. Eng. , Nanjing University , Nanjing 210093 , P. R. China ; Department of Chemistry and Biochemistry , Texas Tech University , Lubbock , TX 79409-1061 , USA . Email: guigen.li@ttu.edu.
authors.forename: Guigen
authors.initials: G
authors.lastname: Li