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Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions

Jean C. Kazmierczak, Roberta Cargnelutti, Thiago Barcellos, Claudio C. Silveira and Ricardo F. Schumacher

Beilstein J. Org. Chem. 2021, 17, 234–244. https://doi.org/10.3762/bjoc.17.24

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Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions

Jean C. Kazmierczak, Roberta Cargnelutti, Thiago Barcellos, Claudio C. Silveira and Ricardo F. Schumacher

Beilstein J. Org. Chem. 2021, 17, 234–244. https://doi.org/10.3762/bjoc.17.24

How to Cite

Kazmierczak, J. C.; Cargnelutti, R.; Barcellos, T.; Silveira, C. C.; Schumacher, R. F. Beilstein J. Org. Chem. 2021, 17, 234–244. doi:10.3762/bjoc.17.24

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TY  - JOUR
A1  - Kazmierczak, Jean C.
A1  - Cargnelutti, Roberta
A1  - Barcellos, Thiago
A1  - Silveira, Claudio C.
A1  - Schumacher, Ricardo F.
T1  - Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodium S-organyl sulfurothioates under basic conditions
JF  - Beilstein Journal of Organic Chemistry
PY  - 2021///
VL  - 17
SP  - 234
EP  - 244
SN  - 1860-5397
DO  - 10.3762/bjoc.17.24
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.17.24
KW  - α-alkylthio esters
KW  - α-alkylthio ketones
KW  - Bunte salts
KW  - C–C bond cleavage
KW  - β-keto esters
N2  - We described herein a selective method to prepare α-organylthio esters and α-organylthio ketones by the reaction of β-keto esters with sodium S-benzyl sulfurothioate or sodium S-alkyl sulfurothioate (Bunte salts) under basic conditions in toluene as the solvent at 100 °C. When 4 equivalents of a base were used, a series of differently substituted α-thio esters were obtained with up to 90% yield. On the other hand, employing 2 equivalents of a base, α-thio ketones were achieved after 18 h under air. Furthermore, after a shorter reaction time, the isolation of keto–enol tautomers was possible, revealing them as significant intermediates for the mechanism elucidation.
ER  -

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Scholarly Works

Moloney, M. G. doi:10.1002/9781119821984.ch1
de Souza, A. A. N.; Bartolomeu, A. d. A.; Brocksom, T. J.; Noël, T.; de Oliveira, K. T. Direct Synthesis of α-Sulfenylated Ketones under Electrochemical Conditions. The Journal of organic chemistry 2022, 87, 5856–5865. doi:10.1021/acs.joc.2c00147
Niedbała, P.; Majdecki, M.; Grodek, P.; Jurczak, J. H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters. Molecules (Basel, Switzerland) 2022, 27, 2508. doi:10.3390/molecules27082508

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