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

• Published in: Journal of the Brazilian Chemical Society Vol. 22; no. 9; pp. 1795 - 1807
• 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: Journal Article
• Language: English
• Published: Sociedade Brasileira de Química 01-09-2011
• Subjects: 2-dihydronaphthalenes; CHEMISTRY, MULTIDISCIPLINARY; hypervalent iodine; indanes; Organic Chemistry; organisk kemi; rearrangements; ring contraction; hypervalent iodine; indanes; 1 , 2-dihydronaphthalenes; ring contraction; rearrangements
• ISSN: 0103-5053; 1678-4790
• DOI: 10.1590/S0103-50532011000900024

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