Electrophilic Activation of 1‐Aryl‐3‐bromo‐2,2‐difluoropropan‐1‐ones by Triflic Acid in Reactions with Arenes

Electrophilic Activation of 1‐Aryl‐3‐bromo‐2,2‐difluoropropan‐1‐ones by Triflic Acid in Reactions with Arenes Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2019, Volume: 2019, Number: 34, Pages: 5905-5911 Pages count : 7 DOI: 10.1002/ejoc.201900975

Authors

Aleksandrova Maiia I. ¹ , Ivanov Alexander Yu. ² , Dilman Alexander D. ³ , Vasilyev Aleksander V. ^4,1

Affiliations

1	Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, 199034 Saint Petersburg, Russia
2	Center for Magnetic Resonance, Research Park, St. Petersburg State University, Universitetskiy pr., 26, 198504 Saint Petersburg, Petrodvoretz, Russia
3	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp., 47, 119991 Moscow, Russia
4	Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, 194021 Saint Petersburg, Russia

The reactions of 1-aryl-3-bromo-2,2-difluoropropan-1-ones [Ar(CO)CF2CH2Br] with various arenes Ar′H in the superacid TfOH at room temperature for 1–7 h result in the formation of products of hydroarylation of the carbonyl group, 1,1-diaryl-3-bromo-2,2-difluoropropan-1-ols [ArAr′C(OH)CF2CH2Br], in yields up to 85 %. The reaction with benzene goes deeper and leads to 1-aryl-3-bromo-2,2-difluoro-1,1-diphenylpropanes [ArCPh2CF2CH2Br] in good yields. Mainly, the bromomethyl group (CH2Br) of starting ketones remains untouched under the superacidic conditions. Cationic intermediates of the reaction have been studied by means of NMR spectroscopy. Plausible reaction mechanism is discussed.

Aleksandrova M.I. , Ivanov A.Y. , Dilman A.D. , Vasilyev A.V.
Electrophilic Activation of 1‐Aryl‐3‐bromo‐2,2‐difluoropropan‐1‐ones by Triflic Acid in Reactions with Arenes
European Journal of Organic Chemistry. 2019. V.2019. N34. P.5905-5911. DOI: 10.1002/ejoc.201900975 WOS Scopus OpenAlex

Web of science:	WOS:000484421500001
Scopus:	2-s2.0-85071603353
OpenAlex:	W2968703961

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