Regioselective C–H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins

Xu, Lu; Kawazu, Ryohei; Song, Jizhou; Yoshigoe, Yusuke; Torigoe, Takeru; Kuninobu, Yoichiro

doi:10.1021/acs.orglett.1c01259

Cited by 13 publications

(5 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, the Kuninobu group reported a regioselective iron‐catalyzed trifluoromethylation of electron‐rich arenes with the Langlois’ reagent and tert ‐butyl hydroperoxide using cyclodextrins as additives, the regioselectivity being increased by the inclusion of the substrate inside the cyclodextrin cavity [194] …”

Section: Trifluoromethylation Of (Hetero)arenesmentioning

confidence: 99%

Direct Perfluoroalkylation of C−H Bonds in (Hetero)arenes

Baguia

Evano

2022

Chemistry A European J

View full text Add to dashboard Cite

Perfluoroalkylated (hetero)arenes represent an extremely important family of molecules commonly utilized in many areas such as medicinal chemistry, agrochemistry and material sciences. Due to their unique properties, they have attracted significant interest from synthetic chemists and various methods have been developed for their synthesis. Among them, the direct perfluoroalkylation of C(sp 2 )À H bonds in (hetero)arenes is one of the most attractive and straightforward ones, provided that it proceeds with high levels of regioselectivity. In this review article, a comprehensive overview of advances in this field is presented, with a special focus on the reaction mechanisms involved in these transformations and their regioselectivity. All methods available have been classified according to the nature of the perfluoroalkyl chain introduced, trifluoromethylation reactions being overviewed in a separate section, and to the nature of the reagents/catalysts required.

show abstract

Section: Trifluoromethylation Of (Hetero)arenesmentioning

confidence: 99%

Direct Perfluoroalkylation of C−H Bonds in (Hetero)arenes

Baguia

Evano

2022

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…However, the addition of β‐cyclodextrin suppressed the formation of the di‐trifluoromethylated product, and the mono‐trifluoromethylated product was obtained with 96 % yield with high mono selectivity (Scheme 9). [17] …”

Section: Inclusion Of Aromatic Substrates Inside the Cavity Of Cyclic...mentioning

confidence: 99%

“…The mixing of the substrate with β-cyclodextrin in H 2 O and the treatment of the mixture with NaO 2 SCF 3 and t BuOOH in the presence of a catalytic amount of FeCl 3 provided the trifluoromethylated product with 91 % yield with high regioselectivity, even on the gram scale (Scheme 8). [17] The regioselectivity was improved dramatically using βcyclodextrin. [17] In the case of 1,3,5-trimethoxybenzene, a mixture of mono-and di-trifluoromethylated products is formed.…”

Section: Inclusion Of Aromatic Substrates Inside the Cavity Of Cyclic...mentioning

confidence: 99%

“…[17] The regioselectivity was improved dramatically using βcyclodextrin. [17] In the case of 1,3,5-trimethoxybenzene, a mixture of mono-and di-trifluoromethylated products is formed. However, the addition of β-cyclodextrin suppressed the formation of the di-trifluoromethylated product, and the monotrifluoromethylated product was obtained with 96 % yield with high mono selectivity (Scheme 9).…”

Section: Inclusion Of Aromatic Substrates Inside the Cavity Of Cyclic...mentioning

confidence: 99%

See 1 more Smart Citation

Regioselective C−H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

Kuninobu

2023

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Fluorinated functional groups, including trifluoromethyl group, play important roles in the development of drugs, agrochemicals, and organic functional materials. Therefore, the development of highly effective and practical reactions to introduce fluorinated functional groups into (hetero)aromatic compounds is highly desirable. We have achieved several regioselective C−H trifluoromethylation and related reactions by electrophilic and nucleophilic activation of six‐membered heteroaromatic compounds and steric protection of aromatic compounds. These reactions proceed in good to excellent yields, even on a gram scale, with high functional group tolerance, and are applicable to the regioselective trifluoromethylation of drug molecules. In this personal account, the background of the introduction reactions of fluorinated functional groups, our reaction designs to achieve regioselective C−H trifluoromethylation and the related reactions of (hetero)aromatic compounds are explained.

show abstract

“… In this context, exploring efficient and practical trifluoromethylation has attracted continuous research interest in recent years . Remarkable achievements in trifluoromethylation of various substrates including (hetero) arenes, alkenes, alkynes, organohalides, arylborons, etc., have been made in the presence of trifluoromethyl sources. The aforementioned protocols usually use [ S -(trifluoromethyl)dibenzothiophenium tetrafluoroborate] (Umemoto reagent), 1-trifluoromethyl-1,2-benziodoxol-3-(1 H )-one (Togni reagent), CF 3 SO 2 Na (Langlois reagent), CF 3 X, TMSCF 3 , and CF 3 SO 2 X as trifluoromethyl sources.…”

Section: Introductionmentioning

confidence: 99%

Fe-Catalyzed Radical Trifluoromethyl-Alkenylation of Alkenes or Alkynes with 2-Amino-1,4-naphthoquinones

Tang

Yang

Zhang³

et al. 2022

J. Org. Chem.

View full text Add to dashboard Cite

The first Fe-catalyzed three-component radical trifluoromethyl-alkenylation of alkenes with 2-amino-1,4-naphthoquinones and CF3SO2Na is reported. The developed reaction enables the highly regioselective preparation of a variety of valuable CF3-substituted 1,4-naphthoquinones in acceptable yields. In the light of the catalytic system, alkynes smoothly afford the corresponding three- or four-component trifluoromethyl-alkenylation products. This protocol features use of easily available and inexpensive reagents, broad substrate scope, and simple reaction conditions.

show abstract

Regioselective C–H Trifluoromethylation of Aromatic Compounds by Inclusion in Cyclodextrins

Cited by 13 publications

References 39 publications

Direct Perfluoroalkylation of C−H Bonds in (Hetero)arenes

Direct Perfluoroalkylation of C−H Bonds in (Hetero)arenes

Regioselective C−H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

Fe-Catalyzed Radical Trifluoromethyl-Alkenylation of Alkenes or Alkynes with 2-Amino-1,4-naphthoquinones

Contact Info

Product

Resources

About