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通过霍纳-瓦兹沃思-埃蒙斯反应高选择性合成(E)-烯基-(五氟硫基)苯。

Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner-Wadsworth-Emmons reaction.

机构信息

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague, Czech Republic.

出版信息

Beilstein J Org Chem. 2012;8:1185-90. doi: 10.3762/bjoc.8.131. Epub 2012 Jul 25.

DOI:10.3762/bjoc.8.131
PMID:23019446
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3458736/
Abstract

Diethyl 2-nitro-(pentafluorosulfanyl)benzylphosphonates, available by the vicarious nucleophilic substitution reaction of meta- and para-nitro-(pentafluorosulfanyl)benzenes and diethyl chloromethylphosphonate, undergo Horner-Wadsworth-Emmons reaction with aldehydes in the presence of potassium hydroxide in acetonitrile at ambient temperature to give (E)-2-nitro-1-alkenyl-(pentafluorosulfanyl)benzenes in good yields and high stereoselectivities. Follow-up transformations of the primary products provided (E)-1-alkenyl-(pentafluorosulfanyl)benzenes and 2-(2-arylethyl)-(pentafluorosulfanyl)anilines.

摘要

2-硝基-(五氟硫基)苄基二乙基膦酸酯可通过间位和对位硝基-(五氟硫基)苯与氯甲基二乙基膦酸酯的替代亲核取代反应得到，在乙腈中，在环境温度下，用氢氧化钾与醛进行 Horner-Wadsworth-Emmons 反应，以良好的产率和高立体选择性得到(E)-2-硝基-1-烯基-(五氟硫基)苯。初级产物的后续转化提供了(E)-1-烯基-(五氟硫基)苯和 2-(2-芳基乙基)-(五氟硫基)苯胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/6bde58dcd685/Beilstein_J_Org_Chem-08-1185-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/5f7251b20101/Beilstein_J_Org_Chem-08-1185-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/e264779df92f/Beilstein_J_Org_Chem-08-1185-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/53d9dd2f2f6e/Beilstein_J_Org_Chem-08-1185-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/33ba1e5f82f2/Beilstein_J_Org_Chem-08-1185-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/6bde58dcd685/Beilstein_J_Org_Chem-08-1185-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/5f7251b20101/Beilstein_J_Org_Chem-08-1185-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/e264779df92f/Beilstein_J_Org_Chem-08-1185-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/53d9dd2f2f6e/Beilstein_J_Org_Chem-08-1185-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/33ba1e5f82f2/Beilstein_J_Org_Chem-08-1185-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/70aa/3458736/6bde58dcd685/Beilstein_J_Org_Chem-08-1185-g006.jpg

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本文引用的文献

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Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry.发现芳基硫五氟化物及其高同系物、双（硫五氟化物）和三（硫五氟化物）的实用生产工艺：“超三氟甲基”芳烃化学及其工业新时代的开端。
Beilstein J Org Chem. 2012;8:461-71. doi: 10.3762/bjoc.8.53. Epub 2012 Mar 29.
3
Preparation of SF5 aromatics by vicarious nucleophilic substitution reactions of nitro(pentafluorosulfanyl)benzenes with carbanions.
硝基金刚烷（五氟硫基）苯通过碳负离子的间接亲核取代反应制备 SF5 芳烃。
J Org Chem. 2011 Jun 3;76(11):4781-6. doi: 10.1021/jo200618p. Epub 2011 May 13.
4
S(N)Ar reactions of nitro-(pentafluorosulfanyl)benzenes to generate SF5 aryl ethers and sulfides.硝-(五氟硫基)苯的 S(N)Ar 反应生成 SF5 芳基醚和硫醚。
Org Lett. 2011 Mar 18;13(6):1466-9. doi: 10.1021/ol2001478. Epub 2011 Feb 22.
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New and convenient method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic organic compounds.将五氟硫烷基（SF5）取代基引入脂肪族有机化合物的新型便捷方法。
Org Lett. 2002 Aug 22;4(17):3013-5. doi: 10.1021/ol026483o.
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