Metal-Free Alpha Trifluoromethylselenolation of Carbonyl Derivatives under Batch and Flow Conditions

Massolo, Elisabetta; Pirola, Margherita; Rossi, Sergio; Benincori, Tiziana

doi:10.3390/molecules24040726

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Article

18 February 2019

8 Pages

Metal-Free Alpha Trifluoromethylselenolation of Carbonyl Derivatives under Batch and Flow Conditions

and

Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy

Dipartimento di Scienza e Alta Tecnologia, Università degli Studi Dell’Insubria, Via Valleggio 11, 22100 Como, Italy

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Molecules2019, 24(4), 726;https://doi.org/10.3390/molecules24040726

This article belongs to the Special Issue Flow Chemistry in Organic Synthesis

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Abstract

Trifluoromethylselenolated carbonyl compounds represent an emerging class with potential applications in several fields; however, a widespread use of such compound is hampered by the very limited number of strategies for their preparation. In this study we developed a method for the preparation of α-SeCF₃ substituted carbonyl derivatives using an in situ generated electrophilic ClSeCF₃ species. We also implemented an in-flow protocol to improve the safety features of the process.

Keywords:

trifluoromethylselenolation; carbonyl compounds; selenium; fluorinated derivatives; flow chemistry

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