A Simple Protocol from Benzalacetones to 1,1,1‐Trifluoro‐2,5‐diketones and 2‐(Trifluoromethyl)furans by Reductive Trifluoroacetylation

A simple two‐step access to 1,1,1‐trifluoro‐2,5‐diketones and 2‐(trifluoromethyl)furans was developed through magnesium‐promoted reductive trifluoroacetylation of benzalacetones and acid‐facilitated deacetalization. Two types of trifluoromethylated compounds were selectively synthesized from easily...

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Veröffentlicht in:European journal of organic chemistry 2020-04, Vol.2020 (15), p.2237-2243
Hauptverfasser: Zhang, Tianyuan, Xie, Chunchao, Sakata, Hiroto, Nakajima, Konomi, Shimoyama, Tatsuya, Watanabe, Tomohiro, Maekawa, Hirofumi
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Sprache:eng
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Zusammenfassung:A simple two‐step access to 1,1,1‐trifluoro‐2,5‐diketones and 2‐(trifluoromethyl)furans was developed through magnesium‐promoted reductive trifluoroacetylation of benzalacetones and acid‐facilitated deacetalization. Two types of trifluoromethylated compounds were selectively synthesized from easily prepared aromatic conjugated enones and ethyl trifluoroacetate by control of reaction conditions in moderate to high yields with wide substrate tolerance. A simple two‐step protocol from aromatic conjugated ketones to 1,1,1‐trifluoro‐2,5‐diketones and 2‐(trifluoromethyl)furans was developed through magnesium‐promoted reductive trifluoroacetylation and acid‐facilitated deacetalization in moderate to high yields with good substrate tolerance. Two kinds of trifluoromethylated compounds were selectively synthesized by control of reaction conditions, respectively.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000160