Ligandless Pentafluoroethylation of Unactivated (Hetero)aryl and Alkenyl Halides Enabled by the Controlled Self-Condensation of TMSCF3-Derived CuCF3 - imarina:6012542
Mestre, Jordi; Castillon, Sergio; Boutureira, Omar (2019). Ligandless Pentafluoroethylation of Unactivated (Hetero)aryl and Alkenyl Halides Enabled by the Controlled Self-Condensation of TMSCF3-Derived CuCF3. Journal Of Organic Chemistry, 84(23), 15087-15097. DOI: 10.1021/acs.joc.9b02001
Paper original source:
Journal Of Organic Chemistry. 84 (23): 15087-15097
Abstract:
Pentafluoroethylation of unactivated C(sp(2))-X bonds (X = I, Br) using a storable, ligandless CuC2F5 reagent prepared by controlled self-condensation of ready available TMSCF3-derived CuCF3 has been developed. A thorough analysis by F-19 NMR and ESI-MS revealed the nature of this reagent in solution. The operational simplicity and robustness of this system enables the efficient, late-stage incorporation of C2F5 units into a variety of (hetero)aryl and complex alkenyl halides such as glycals, nucleosides, and nucleobases.
Pentafluoroethylation of unactivated C(sp(2))-X bonds (X = I, Br) using a storable, ligandless CuC2F5 reagent prepared by controlled self-condensation of ready available TMSCF3-derived CuCF3 has been developed. A thorough analysis by F-19 NMR and ESI-MS revealed the nature of this reagent in solution. The operational simplicity and robustness of this system enables the efficient, late-stage incorporation of C2F5 units into a variety of (hetero)aryl and complex alkenyl halides such as glycals, nucleosides, and nucleobases.
Title:
Ligandless Pentafluoroethylation of Unactivated (Hetero)aryl and Alkenyl Halides Enabled by the Controlled Self-Condensation of TMSCF3-Derived CuCF3
Química Analítica i Química Orgànica Universitat Rovira i Virgili
Subject:
Chemistry, Organic,Organic Chemistry Trifluoromethylation Reagent Perfluoroalkylation Organic fluorine-compounds Fluoroalkylation reactions Copper Complexes Arylboronic acids Aryl iodides Aqueous-media Química Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ensino Engenharias iv Engenharias ii Engenharias i Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Astronomia / física 00223263