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

Journal of the Brazilian Chemical Society

Fernanda A Siqueira²  Eloisa E Ishikawa²  André Fogaça²  Andréa T Faccio²  Vânia M. T Carneiro²  Rafael R. S Soares²  Aline Utaka²  Iris R. M Tébéka²  Marcin Bielawski²  Berit Olofsson¹  Luiz F Silva Jr² 

[1] ,Universidade de São Paulo Instituto de Química Departamento de Química FundamentalSão Paulo SP ,Brazil

关键词: indanes;    hypervalent iodine;    ring contraction;    1;    2-dihydronaphthalenes;    rearrangements;   

DOI  :  10.1590/S0103-50532011000900024

来源: SciELO

【 摘 要 】

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

【 授权许可】

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