New Protocol for the Synthesis of S-Thioesters from Benzylic, Allylic and Tertiary Alcohols with Thioacetic Acid.
alcohol
kinetics
mechanism
thioesterification
thiol
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
12 Oct 2023
12 Oct 2023
Historique:
received:
05
08
2023
pubmed:
12
10
2023
medline:
12
10
2023
entrez:
12
10
2023
Statut:
aheadofprint
Résumé
A new one-pot solvent-less reaction to convert benzylic, allylic, ferrocenyl or tertiary alcohols into S-thioesters, bench-stable and less odorous precursors of the corresponding thiols, which is based on reactions in neat thioacetic acid in the presence of tetrafluoroboric acid, is presented. Reaction monitoring by NMR and GC of the benzyl alcohol conversion indicated the intermediate formation of benzyl acetate and benzyl thionoacetate (PhCH
Identifiants
pubmed: 37823749
doi: 10.1002/chem.202302551
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202302551Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
J. Clayden, P. MacLellan, Beilstein J. Org. Chem. 2011, 7, 582-595;
I. Shcherbakova, I. Pozharskii in Alkyl Chalcogenides: Sulfur-based Groups, 2005, pp. 89-235;
A. Roland, R. Schneider, A. Razungles, F. Cavelier, Chem. Rev. 2011, 111, 7355-7376.
M. Biosca, M. Coll, F. Lagarde, E. Brémond, L. Routaboul, E. Manoury, O. Pàmies, R. Poli, M. Diéguez, Tetrahedron 2016, 72, 2623-2631.
G. Hellmann, A. Hack, E. Thiemermann, O. Luche, G. Raabe, H. J. Gais, Chem. Eur. J. 2013, 19, 3869-3897.
T. Nishio, J. Chem. Soc. Perkin Trans. 1 1993, 1113-1117.
F. Olivito, P. Costanzo, M. L. Di Gioia, M. Nardi, M. Oliverio, A. Procopio, Org. Biomol. Chem. 2018, 16, 7753-7759;
B. P. Bandgar, V. S. Sadavarte, Synlett 2000, 908-910.
Z. Yang, J. Zhou, J. Am. Chem. Soc. 2012, 134, 11833-11835.
C. J. Ahn, R. Correia, P. DeShong, J. Org. Chem. 2002, 67, 1751-1753.
K. Yamada, K. Nakazono, T. Yoshie, M. Fukuchi, T. Kitaura, T. Takata, Solid State Nucl. Magn. Reson. 2019, 101, 110-115.
C.-H. Lee, S.-M. Lee, B.-H. Min, D.-S. Kim, C.-H. Jun, Org. Lett. 2018, 20, 2468-2471.
A. Bugaut, K. Jantos, J. L. Wietor, R. Rodriguez, J. K. M. Sanders, S. Balasubramanian, Angew. Chem. Int. Ed. 2008, 47, 2677-2680.
L. Routaboul, S. Vincendeau, J.-C. Daran, E. Manoury, Tetrahedron: Asymmetry 2005, 16, 2685-2690;
R. Malacea, E. Manoury, L. Routaboul, J.-C. Daran, R. Poli, J. P. Dunne, A. C. Withwood, C. Godard, S. B. Duckett, Eur. J. Inorg. Chem. 2006, 1803-1816;
E. Le Roux, R. Malacea, E. Manoury, R. Poli, L. Gonsalv, M. Peruzzini, Adv. Synth. Catal. 2007, 349, 309-313.
R. Bouchene, J.-C. Daran, R. Poli, E. Deydier, S. Bouacida, E. Manoury, Inorg. Chim. Acta 2017, 470, 365-372.
A. Z. Kreindlin, F. M. Dolgushin, A. I. Yanovsky, Z. A. Kerzina, P. V. Petrovskii, M. I. Rybinskaya, J. Organomet. Chem. 2000, 616, 106-111.
T. Kim, R. S. Assary, H. Kim, C. L. Marshall, D. J. Gosztola, L. A. Curtiss, P. C. Stair, Catal. Today 2013, 205, 60-66.
M. A. Shalaby, H. Rapoport, J. Org. Chem. 1999, 64, 1065-1070.
G. Levesque, A. Mahjoub, A. Thuillier, Tetrahedron Lett. 1978, 3847-3848;
S. Kato, H. Shibahashi, T. Katada, T. Takagi, I. Noda, M. Mizuta, M. Goto, Liebigs Ann. Chem. 1982, 1229-1244.
J. Grote, F. Friedrich, K. Berthold, L. Hericks, B. Neumann, H. G. Stammler, N. W. Mitzel, Chem. Eur. J. 2018, 24, 2626-2633.
J. Houben, H. Pohl, Ber. Dtsch. Chem. Ges. 1907, 40, 1303.
K. Hartke, N. Rettberg, D. Dutta, H. D. Gerber, Liebigs Ann. Chem. 1993, 1081-1089.
J. Pickardt, N. Rautenberg, Z. Naturforsch. B 1986, 41, 409-412.
A. Fredga, H. Bauer, Ark. Kemi 1950, 2, 113;
G. Szasz, A. Kovacs, I. Hargittai, I. Jeon, G. P. Miller, J. Phys. Chem. A 1998, 102, 484-489.
K. Olsson, H. Baeckstrom, R. Engwall, Ark. Kemi 1966, 26, 219.
N. Mateus, L. Routaboul, J. C. Daran, E. Manoury, J. Organomet. Chem. 2006, 691, 2297-2310.
C. Y. Zhao, L. G. Li, Q. R. Liu, C. X. Pan, G. F. Su, D. L. Mo, Org. Biomol. Chem. 2016, 14, 6795-6803.
J. McNulty, K. Keskar, Eur. J. Org. Chem. 2012, 2012, 5462-5470.
A. J. Neuvonen, T. Földes, A. Madarász, I. Pápai, P. M. Pihko, ACS Catal. 2017, 7, 3284-3294.
K. M. Wager, M. H. Daniels, Org. Lett. 2011, 13, 4052-4055.
E. K. Ryu, Y. S. Choe, S. S. Byun, K. H. Lee, D. Y. Chi, Y. Choi, B. T. Kim, Bioorg. Med. Chem. 2004, 12, 859-864.
T. Castanheiro, A. Schoenfelder, J. Suffert, M. Donnard, M. Gulea, C. R. Chim. 2017, 20, 624-633.
N. Ghaffari Khaligh, RSC Adv. 2013, 3, 99-110.
X. J. Huang, B. Fulton, K. White, A. Bugarin, Org. Lett. 2015, 17, 2594-2597.
S. Divekar, M. Safi, M. Soufiaoui, D. Sinou, Tetrahedron 1999, 55, 4369-4376.
B. T. Holmes, A. W. Snow, Tetrahedron 2005, 61, 12339-12342.
T. C. Pijper, J. Robertus, W. R. Browne, B. L. Feringa, Org. Biomol. Chem. 2015, 13, 265-268.
B.-S. Park, W. Widger, H. Kohn, Bioorg. Med. Chem. 2006, 14, 41-61.
M. D. Rozwadowska, Tetrahedron 1997, 53, 10615-10622.
G. M. Sheldrick, Acta Crystallogr. Sect. A 2015, 71, 3-8.
G. M. Sheldrick, Acta Crystallogr. Sect. C 2015, 71, 3-8.
M. N. Burnett, C. K. Johnson, ORTEPIII, Report ORNL-6895., Oak Ridge National Laboratory, Oak Ridge, Tennessee, U. S., 1996, p;
L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian 16, Revision C.01, Gaussian, Inc., Wallingford CT, 2016, p.
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378-6396.
V. S. Bryantsev, M. S. Diallo, W. A. Goddard III, J. Phys. Chem. B 2008, 112, 9709-9719.