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

Journal of the Brazilian Chemical Society

Carneiro, Vânia M. T¹  Fogaça, André¹  Faccio, Andréa T¹  Siqueira, Fernanda A¹  Bielawski, Marcin¹  Universidade de São Paulo, São Paulo, Brazil¹  Ishikawa, Eloisa E¹  Stockholm University, Stockholm, Sweden¹  Olofsson, Berit¹  Utaka, Aline¹  Tébéka, Iris R. M¹  Silva Jr, Luiz F¹  Soares, Rafael R. S¹ 

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

DOI  :  10.1590/S0103-50532011000900024

学科分类：化学（综合）

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】

Unknown