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Synlett 2019; 30(07): 777-782
DOI: 10.1055/s-0037-1610347
DOI: 10.1055/s-0037-1610347
synpacts
New Avenues in Radical Trifluoromethylselenylation with Trifluoromethyl Tolueneselenosulfonate
C.G. held a doctoral fellowship from la region Auvergne Rhône Alpes. The authors are grateful to the CNRS, ICBMS (UMR 5246), ICL (Institut de Chimie de Lyon) for financial support. The French Fluorine Network as well as the federation RENARD are also acknowledged for their support.Further Information
Publication History
Received: 18 October 2018
Accepted after revision: 12 November 2018
Publication Date:
11 December 2018 (online)
Published as part of the Special Section 10th EuCheMS Organic Division Young Investigator Workshop
Abstract
We demonstrated that the shelf-stable reagent trifluoromethyl tolueneselenosulfonate can be involved in radical trifluoromethylselenylation. Upon visible-light irradiation, the homolysis of the reagent could take place at room temperature. This finding is explored for unprecedented C(sp2)–SeCF3 and C(sp3)–SeCF3 processes under transition-metal-free conditions. Mechanistic investigations, including cyclic voltammetry, luminescence measurement, and EPR studies, allowed the proposal of plausible mechanisms.
1 Introduction.
2 Reactivity of Reagent I with Diazonium Salts
3 Reactivity of Reagent I with Alkenes and Alkynes
4 Conclusion
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