SUPPORTING INFORMATION Polar Organometallic Reagents in ... · One-Pot Sustainable Synthesis of Tertiary Alcohols by Combining Ruthenium-Catalyzed Isomerization of Allylic Alcohols
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SUPPORTING INFORMATION
One-Pot Sustainable Synthesis of Tertiary Alcohols by Combining Ruthenium-
Catalyzed Isomerization of Allylic Alcohols and Chemoselective Addition of
Polar Organometallic Reagents in Deep Eutectic Solvents
Luciana Cicco,a María J. Rodríguez-Álvarez,b Filippo M. Perna,a Joaquín García-Alvarezb,* and Vito Capriatia,*
a Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125, Bari, Italy.
b Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC). Departamento de Química Orgánica e Inorgánica (IUQOEM), Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Química, Universidad de Oviedo, E-33071, Oviedo, Spain
1H and 13C NMR spectra of 3-phenyl-heptan-3-ol (3a)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
OH
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1H and 13C NMR spectra of 1-methyl-1'-phenyl-propan-1-ol (3b)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
OH
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1H and 13C NMR spectra of 4-methyl-3-phenyl-hexan-3-ol (3c)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
OH
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1H spectra of 1,1-diphenyl-propan-1-ol (3d)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
OH
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1H and 13C spectrum of 3-(2-methoxyphenyl)heptan-3-ol (3f)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OCH3
OH
OCH3
OH
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1H and 13C NMR spectra of 3-(p-tolyl)heptan-3-ol (3g)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
H3C
OH
H3C
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1H and 13C NMR spectra of 3-(4-bromophenyl)heptan-3-ol (3h)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
Br
OH
Br
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1H and 13C NMR spectra of 3-(naphthalen-1-yl)heptan-3-ol (3i)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
HO
HO
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1H spectrum of 3-methyl-octan-3-ol (3j)
1H NMR 400MHz, CDCl3
13C NMR 400MHz, CDCl3
OH
OH
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5. References
[1] M. Lafrance, M. Roggen, E. M. Carreira, Angew. Chem. 2012, 124, 3527–3530; Angew. Chem. Int. Ed. 2012, 51, 3470–3473.
[2] (a) B. Skillinghaug, C. Skoeld, J. Rydfjord, F. Svensson, M. Behrends, J. Saevmarker, P. J. R. Sjoeberg, M. Larhed, J. Org. Chem. 2014, 79, 12018–12032; (b) Y. Li, D. Xue, W. Lu, C. Wang, Z.-T. Liu, J. Xiao, Org. Lett. 2014, 16, 66–69; (c) A. Borah, L. Goswami, K. Neog, P. Gogoi, J. Org. Chem. 2015, 80, 4722–4728; (d) E. Erbing, A. Vázquez-Romero, A. Bermejo Gómez, A. E. Platero-Prats, F. Carson, X. Zou, P. Tolstoy, B. Martín-Matute, Chem. Eur. J. 2016, 22, 15659–15663.
[3] (a) G. Huelgas, L. K. LaRochelle, L. Rivas, Y. Luchinina, R. A. Toscano, P. J. Carroll, P. J. Walsh, C. Anaya de Parrodi, Tetrahedron, 2011, 67, 4467–4474; (b) Y.-X. Liao, C.-H. Xing, Q.-S. Hu, Org. Lett. 2012, 14, 1544–1547.