HFO-1234yf as a CF3-building block: Synthesis of trifluoromethyl-benzophenone derivatives by deoxygenative aromatisation

被引：4

作者：

Murray, Ben J. ^{[1
]}

Boulton, Lee T. ^{[2
]}

Sandford, Graham ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, South Rd, Durham DH1 3LE, England

[2] GlaxoSmithKline Res & Dev Ltd, Med Res Ctr, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2021年 / 245卷

基金：

英国工程与自然科学研究理事会;

关键词：

Trifluoromethyl ynone; HFO-1234yf; Trifluoromethyl benzophenone; Aromatisation; Cycloaddition; DIELS-ALDER REACTION; SANDMEYER TRIFLUOROMETHYLATION; METAL-FREE; CYCLOTRIMERIZATION; FACILE;

D O I：

10.1016/j.jfluchem.2021.109774

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Trifluoromethyl ynones derived from the 4th generation refrigerant 2,3,3,3-tetrafluoropropene (HFO-1234yf) undergo rapid Diels-Alder cycloaddition reactions with furans in near quantitative yields. Subsequent deoxygenation of the resulting oxabicyclic adducts leads to formation of ortho-trifluoromethylbenzophenones in generally good yields without the need for purification by column chromatography. Complete selectivity for a single regioisomer was observed in all cases. This method provides a new route from an inexpensive feedstock to highly substituted CF3-aromatic systems that can be difficult to access selectively by established methods.

引用

页数：5

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