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Paper | Special issue | Vol 64, No. 1, 2004, pp.199-206
Published online, 1st July, 2004
DOI: 10.3987/COM-04-S(P)12
Diels-Alder Reaction and Double Phenylation in Reaction of Thiophenes with Diphenyliodonium Triflate

Bian-Xiang Zhang, Takato Nuka, Yuzo Fujiwara, Teizo Yamaji, Zhaomin Hou, and Tsugio Kitamura*

*Faculty of Science and Engineering, Saga University, Honjo 1, Saga, Saga 840-8502, Japan


The reaction of 2,5-dimethylthiophene with diphenyliodonium triflate in the presence of N-phenylmaleimide and a catalytic amount of Cu(OAc)2 gave 1:1 and 1:2 cycloadducts with N-phenylmaleimide. The similar reactions of 2,5-bis(trimethylsilyl)thiophene, 3-phenylthiophene, and thiophene afforded 2,5-diphenylthiophene, 2,3,5-triphenylthiophene, and 2,5-diphenylthiophene, respectively. The cycloadducts and 2,5-diphenylated thiophenes are considered to be formed via S-phenylation of thiophenes affording 1-phenylthiophenium triflates.