Fluoroalcohols: Efficient Solvents for the Iodine(III)-Promoted Oxidative Rearrangement of 1,2-Dihydronaphthalenes

Fluoroalcohols: Efficient Solvents for the Iodine(III)-Promoted Oxidative Rearrangement of 1,2-Dihydronaphthalenes

Ishikawa, Eloisa E.; Fogaça, André; Faccio, Andréa T.; Carneiro, Vânia M. T.; Utaka, Aline; Tébéka, Iris R. M.; Bielawski, Marcin; Olofsson, Berit; Jr., Luiz F. Silva

Abstract:

Hypervalent iodine reagents have a key role in chemical synthesis. Since the first report, CF3CH2OH (TFE) and (CF3)2CHOH (HFIP) have been used as solvent in reactions with hypervalent iodine compounds. However, TFE and HFIP have not been used in the rearrangement of alkenes. We reported the ring contraction of 1,2-dihydronaphthalenes in MeOH or in MeCN mediated by PhI(OH)OTs (HTIB). Herein we describe fluoroalcohols as a great alternative for the oxidative rearrangement of alkenes mediated by HTIB. Some of the results in this work were already presented, and they are shown here for comparison.

Hypervalent iodine reagents have a key role in chemical synthesis. Since the first report, CF3CH2OH (TFE) and (CF3)2CHOH (HFIP) have been used as solvent in reactions with hypervalent iodine compounds. However, TFE and HFIP have not been used in the rearrangement of alkenes. We reported the ring contraction of 1,2-dihydronaphthalenes in MeOH or in MeCN mediated by PhI(OH)OTs (HTIB). Herein we describe fluoroalcohols as a great alternative for the oxidative rearrangement of alkenes mediated by HTIB. Some of the results in this work were already presented, and they are shown here for comparison.

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DOI: 10.5151/chempro-14bmos-R0212-1

Referências bibliográficas

• [1] 1 Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. 2 Yakura, T.; Tohma, H.; Kikuchi, K.; Tamura, Y. Tetrahedron Lett. 1989, 30, 1119. 3 Silva, L. F., Jr.; Siqueira, F. A.; Pedrozo, E. C.; Vieira, F. Y. M.; Doriguetto, A. C. Org. Lett. 2007, 9, 1433; 4a Silva Jr., L. F.; Ishikawa, E. E.; Almeida Neto, A. F.; Carneiro, V. M. T.; 32thRASBQ 2009, QO-126. 4b Faccio, A. T.; Carneiro, V. M. T.; Silva Jr., L. F.; 33thRASBQ 2010, ORG-019.

Como citar:

Ishikawa, Eloisa E.; Fogaça, André; Faccio, Andréa T.; Carneiro, Vânia M. T.; Utaka, Aline; Tébéka, Iris R. M.; Bielawski, Marcin; Olofsson, Berit; Jr., Luiz F. Silva; "Fluoroalcohols: Efficient Solvents for the Iodine(III)-Promoted Oxidative Rearrangement of 1,2-Dihydronaphthalenes", p-212-212. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0212-1