Novel synthesis of perfluoroalkylated heterocyclic compounds from α-chlorostyrenes via perfluoroalkylated α,β-unsaturated ketones

Ohkoshi, Masanori; Yoshida, Masato; Matsuyama, Haruo; Iyoda, Masahiko

doi:10.1016/s0040-4039(00)01871-2

Cited by 18 publications

(11 citation statements)

References 7 publications

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“…69 The authors do not provide an explanation for this observation. The reactivity of these arenes in the production of peruorohexylated arenes is consistent with the electrophilicity of the peruoroalkyl radical.…”

Section: Transition Metal Photocatalyzed Peruoroalkylation Of Arenesmentioning

confidence: 87%

Perfluoroalkylation reactions of (hetero)arenes

2015

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Perfluoroalkylation reactions of arenes have not been the subject of intense study as has been the case for the trifluoromethylation reactions of aromatics. However, the new synthetic methods proposed for achieving homolytic aromatic substitution reactions with perfluoroalkyl moieties have begun to claim a relevant role in functionalization reactions, as revealed by the interesting properties of arenes with large perfluoroalkyl chains. Methods for achieving Ar-R f bonding reactions can be classified into thermal and photochemical, which can in turn make use of transition metals or be non-metal catalyzed. Reactions are mainly radical in nature. Radical methods for introducing R f moieties into arenes have resulted as being the most popular and versatile options available to synthetic chemists.Scheme 3 Thermal radical perfluoroalkylation of arenes.Scheme 4 Perfluoroalkylation of heteroarenes employing perfluorocarboxylic anhydrides.Scheme 5 Perfluoroalkylation of dinitrobenzenes. 62500 | RSC Adv., 2015, 5, 62498-62518 This journal is Scheme 29 Lewis acid-mediated perfluoroalkylation of (hetero)arenes in the presence of IF 5 . Scheme 30 Perfluoroalkylation of arenes. This journal isScheme 38 Scope of the PET perfluoroalkylation of N,N-disubstituted aromatic amines.Scheme 39 Proposed mechanism for the PET perfluoroalkylation of N,N-disubstituted aromatic amines.Scheme 40 Photoinduced perfluorobutylation of (di)benzo(hetero)arenes. This journal isScheme 41 Proposed mechanism for the perfluorobutylation of dibenzoheteroarenes in aqueous mixtures.Scheme 42 Scope of the Ti-photocatalyzed reaction of arenes. Scheme 43 Proposed TiO 2 -photocatalyzed perfluoroalkylation of arenes. Scheme 44 Generation of perfluoroalkyl radicals by TiO 2 -photocatalyzed one electron reduction of perfluoroalkyliodides. 62514 | RSC Adv., 2015, 5, 62498-62518 This journal is Scheme 45 TiO 2 -photocatalytic aromatic perfluoroalkylations of p-xylene.Scheme 46 Direct C-H difluoromethylenephosphonation of (hetero) arenes.Scheme 47 Mechanism proposed for the direct C-H difluoromethylenephosphonation of (hetero)arenes. This journal is

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Section: Transition Metal Photocatalyzed Peruoroalkylation Of Arenesmentioning

confidence: 87%

Perfluoroalkylation reactions of (hetero)arenes

2015

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“…The trichloromethyl group is the carboxyl group precursor: using water as solvent it leads to the formation of carboxylic acids whereas the use of an alcohol leads to ester derivatives. In contrast, the b-perfluoroalkyl-b-alkoxyvinyl phenyl ketone undergoes a selective attack on the carbonyl group upon reacting with hydroxylamine in basic medium, affording an isoxazole bearing a perfluoroalkyl substituent (Table 9.5, entry 7) [109].…”

Section: Tautomerismmentioning

confidence: 99%

Five‐Membered Heterocycles: 1,2‐Azoles. Part 2. Isoxazoles and Isothiazoles

Silva

Tomé

Melo

et al. 2011

Modern Heterocyclic Chemistry

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“…There was no report on the synthesis of b-alkynyl-btrifluoromethylated enones. Although addition-elimination reactions of b-trifluoromethylated enaminones [12][13][14][15] or b-chloro (or fluoro)-b-trifluoromethylated enones [4][5]24] with heteroatom nucleophiles (N, O, S) have been well established in the previous literatures, there was no report on the addition-elimination reactions of b-trifluoromethylated enaminones or b-chloro-b-trifluoromethylated enones with carbon nucleophiles such as Grignard reagents or organolithium reagents. Therefore, we first examined on the reaction of 1a with phenyllithium.…”

Section: Preparation Of B-aryl (Or Alkynyl)-btrifluoromethylated Enonmentioning

confidence: 99%