METHYL 2-(ACETYLTHIO)ACETATE

Methyl 2-(methylthio)acetate

• Molecular FormulaC4H8O2S
• Average mass120.170 Da
• 16630-66-3
• S-Methylthioglycolate

DOI: 10.1021/acs.oprd.7b00378

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This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Krzysztof Kuciński*  and Grzegorz Hreczycho* 

Faculty of Chemistry, Adam Mickiewicz University in Poznań, ul. Umultowska 89b, 61-614 Poznań, Poland

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.7b00378

Publication Date (Web): March 12, 2018

Copyright © 2018 American Chemical Society

*E-mail: kucinski.k@amu.edu.pl., *E-mail: g.h@amu.edu.pl. Web: http://ghgroup.home.amu.edu.pl.

 

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Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

Green Chem., 2018, 20,973-977
DOI: 10.1039/C7GC03719H, Communication

Fuhong Xiao, Chao Liu, Dahan Wang, Huawen Huang, Guo-Jun Deng
A three starting material four component reaction (3SM-4CR) strategy is described to prepare [small beta]-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system.

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 

Fuhong Xiao,*^a  Chao Liu,^a  Dahan Wang,^a  Huawen Huang^a  and  Guo-Jun Deng*^a 

Author affiliations

* Corresponding authors

^a Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Xiangtan 411105, China
E-mail: fhxiao@xtu.edu.cn, gjdeng@xtu.edu.cn

Abstract

A three starting material four component reaction (3SM-4CR) strategy is described to prepare β-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system. In this process, DMA was used as a dual synthon to provide two carbons. A broad range of functional groups were tolerated in this reaction system.

 1-phenyl-2-(tosylmethyl)prop-2-en-1-one (3ab)

 

43.2 mg, 72% yield).

 

1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 8.2 Hz, 2H), 7.68-7.65 (m, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.8 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H), 6.25 (s, 1H), 6.02 (s, 1H), 4.35 (s, 2H), 2.39 (s, 3H).

 

13C NMR (100 MHz, CDCl3) δ 194.7, 144.9, 136.1, 135.8, 135.7, 133.9, 132.6, 129.8, 129.6, 128.3, 128.2, 57.7, 21.6.

 

HRMS calcd. for: C17H17O3S+ [M+H]+ 301.08929, found 301.08908

 

 

1H NMR PREDICT

13C NMR PREDICT ABOVE

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Cc1ccc(cc1)S(=O)(=O)CC(=C)C(=O)c2ccccc2

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p-Aminophenol

 

p-Aminophenol [123-30-8].

M.p. 182 °C; 1H NMR (300 MHz, d6-DMSO): 4.37 (br s, 2H, NH2), 6.37-6.44 (m, 2HAr), 6.44-6.50 (m, 2HAr), 8.33 (br s, 1H, OH);

13C NMR (75 MHz, d6-DMSO): δ 115.2 (2 CHAr), 115.5 (2 CHAr), 140.7 (Cq Ar), 148.2 (Cq Ar);

IR (ATR) max: 3338, 3279, 1471; MS (ESI+ ): 110.1 ([M+H]+ , 100).

1D 1H ABOVE

2D [1H,1H]-TOCSY ABOVE

1D 13C ABOVE

1D DEPT90 ABOVE

1D DEPT135 ABOVE

2D [1H,13C]-HSQC ABOVE

2D [1H,13C]-HMBC ABOVE

A sustainable procedure toward alkyl arylacetates: palladium-catalysed direct carbonylation of benzyl alcohols in organic carbonates

A sustainable procedure toward alkyl arylacetates: palladium-catalysed direct carbonylation of benzyl alcohols in organic carbonates

Green Chem., 2018, Advance Article
DOI: 10.1039/C7GC03619A, Communication

Yahui Li, Zechao Wang, Xiao-Feng Wu
A sustainable procedure for the synthesis of various alkyl arylacetates from benzyl alcohols has been developed

 

A sustainable procedure toward alkyl arylacetates: palladium-catalysed direct carbonylation of benzyl alcohols in organic carbonates

 

Yahui Li,^a  Zechao Wang^a  and  Xiao-Feng Wu*^ab 

Author affiliations

* Corresponding authors

^a Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany

^b Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Campus, Hangzhou 310018, People's Republic of China
E-mail: Xiao-Feng.Wu@catalysis.de

Abstract

A sustainable procedure for the synthesis of various alkyl arylacetates from benzyl alcohols has been developed. With palladium as the catalyst and organic carbonates as the green solvent and in situ activator, benzyl alcohols were carbonylated in an efficient manner without any halogen additives.

Ethyl 2-phenylacetate
1H NMR (300 MHz, Chloroform-d) δ 7.32 – 7.08 (m, 5H), 4.08 (q, J = 7.1 Hz, 2H), 3.54 (s, 2H), 1.18 (t, J = 7.1 Hz, 3H).
13C NMR (75 MHz, CDCl3) δ 171.61, 134.17, 129.24, 128.54, 127.03, 60.85, 41.45, 14.18.

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