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

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

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, CH3CN, 2 , 2, 2-trifluoroethanol (TFE), 1 , 1, 1, 3, 3, 3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1, 3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry

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Bibliographic Details
Main Authors: Siqueira,Fernanda A, Ishikawa,Eloisa E, Fogaça,André, Faccio,Andréa T, Carneiro,Vânia M. T, Soares,Rafael R. S, Utaka,Aline, Tébéka,Iris R. M, Bielawski,Marcin, Olofsson,Berit, Silva Jr,Luiz F
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2011
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000900024
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