Metal-free synthesis of indanes by iodine (III)-mediated ring contraction of 1, 2-dihydronaphthalenes

FA Siqueira, EE Ishikawa, A Fogaça…

Index: Siqueira, Fernanda A.; Ishikawa, Eloisa E.; Fogaca, Andre; Faccio, Andrea T.; Carneiro, Vania M. T.; Soares, Rafael R. S.; Utaka, Aline; Tebeka, Iris R. M.; Bielawski, Marcin; Olofsson, Berit; Silva Jr., Luiz F. Journal of the Brazilian Chemical Society, 2011 , vol. 22, # 9 p. 1795 - 1807

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Citation Number: 26

Abstract

ABSTRACT A metal-free protocol was developed to synthesize indanes by ring contraction of 1, 2-dihydronaphthalenes promoted by PhI (OH) OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH 3 CN, 2, 2, 2- trifluoroethanol (TFE), 1, 1, 1, 3, 3, 3-hexafluoroisopropanol (HFIP), and a 1: 4 mixture of TFE: CH 2 Cl 2) under mild conditions. The ring contraction diastereoselectively gives ...