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

Article abstract of 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. ?2011 Sociedade Brasileira de Qui?mica.