A new and efficient hypervalent iodine-benzyne precursor,(phenyl)[o-(trimethylsilyl) phenyl] iodonium triflate: Generation, trapping reaction, and nature of benzyne

…, K Inoue, M Todaka, N Fukatsu, Z Meng…

Index: Kitamura, Tsugio; Yamane, Masakatsu; Inoue, Kensuke; Todaka, Mitsuru; Fukatsu, Norihiko; Meng, Zhaohong; Fujiwara, Yuzo Journal of the American Chemical Society, 1999 , vol. 121, # 50 p. 11674 - 11679

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Citation Number: 138

Abstract

A new and efficient hypervalent iodine-benzyne precursor,(phenyl)[2-(trimethylsilyl) phenyl] iodonium triflate (10), is reported. The hypervalent iodine-benzyne precursor 10 is readily prepared by reaction of 1, 2-bis (trimethylsilyl) benzene with a PhI (OAc) 2/TfOH reagent system. Treatment of 10 with Bu4NF in CH2Cl2 at room temperature gives high yields of the benzyne adducts in the presence of a trapping agent such as furan, 2-methylfuran, ...