Formation of Quaternary Carbon Center with a Trifluoromethyl Group Using a Pd-Catalyzed Allylation Reaction

Sato, Kazuyuki; Takiguchi, Yu; Yoshizawa, Yosuke; Iwase, Kayoko; Shimizu, Yoshie; Tarui, Atsushi; Omote, Masaaki; Kumadaki, Itsumaro; Andõ, Akira

doi:10.1248/cpb.55.1593

CHEMICAL & PHARMACEUTICAL BULLETIN

2007

DOI: 10.1248/cpb.55.1593

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Formation of Quaternary Carbon Center with a Trifluoromethyl Group Using a Pd-Catalyzed Allylation Reaction

Kazuyuki Sato

Yu Takiguchi

Yosuke Yoshizawa

et al.

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Cited by 15 publications

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“…Furthermore, a Pd-catalyzed defluorination/arylation process can be employed to afford fluorinated-α,β-unsaturated ketone 46 . Moreover, a trifluoromethylated quaternary center was easily constructed via the allylation of the ketone in good yield ( 47 ) …”

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Selectively Tunable Synthesis of α-Trifluoromethyl Ketones

Zhou

Lü

et al. 2023

Org. Lett.

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A cross-coupling of aldehydes and α-trifluoromethyl alkyl bromides was developed via dual nickel/photoredox catalysis system. A wide variety of substrates bearing a diverse set of functional groups were compatible to afford α-trifluoromethyl ketones under very mild conditions (visible light, ambient temperature, no strong base). Selectively tunable access to these ketones with the trifluoromethyl group on any one side can be smoothly obtained by simply modulating different reagents. Meanwhile, the asymmetric pattern was also investigated.G iven the incorporation of a trifluoromethyl group into molecules can significantly change their lipophilicity, metabolic stability, and many other properties, 1 considerable achievements have been made in the development of novel synthetic routes to trifluoromethylated skeletons. 2 Among them, due to the great versatility of carbonyls, much attention has been paid to α-CF 3 carbonyl compounds. One of the most efficient and well-known protocols to deliver these types of products is electrophilic trifluoromethylation. 3 However, compared with the trifluoromethylation of aldehydes, 4 esters, 5 and amides, 6 the process with ketones faces many issues, especially for the ketones with two kinds of α hydrogen atoms which would lead to a mixture in the enolate process 7 (Scheme 1 top). Therefore, developing a high-selectivity and tunable method to afford the α-CF 3 ketones is still very practical and rewarding.Very recently, a cross-coupling of α-trifluoromethyl alkyl bromides and aryl halides to deliver benzylic trifluoromethylation products under dual nickel/photoredox catalysis system has been developed in our group. 8,9 Considering that

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confidence: 99%

Selectively Tunable Synthesis of α-Trifluoromethyl Ketones

Zhou

Lü

et al. 2023

Org. Lett.

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Construction of Trifluoromethyl‐Bearing Quaternary Carbon Centers by Intramolecular Decarboxylative Allylation of α‐Trifluoromethyl β‐Keto Esters

et al. 2011

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International audienceA new palladium-catalyzed decarboxylative allylation of allyl α-trifluoromethyl-β-keto esters was developed in the presence of tris(dibenzylideneacetone)dipalladium [Pd2(dba)3] and 1,2-bis(diphenylphosphino)ethane (dppe) in THF. α-Trifluoromethyl ketones featuring a quaternary carbon center were produced in good yields and the dreaded α,β-unsatd.-β,β-difluoro ketones resulting from β-elimination of a fluoride ion were not obsd

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ChemInform Abstract: Formation of Quaternary Carbon Center with a Trifluoromethyl Group Using a Pd‐Catalyzed Allylation Reaction.

et al. 2008

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Formation of Quaternary Carbon Center with a Trifluoromethyl Group Using a Pd-Catalyzed Allylation Reaction

Cited by 15 publications

References 18 publications

Selectively Tunable Synthesis of α-Trifluoromethyl Ketones

Selectively Tunable Synthesis of α-Trifluoromethyl Ketones

Construction of Trifluoromethyl‐Bearing Quaternary Carbon Centers by Intramolecular Decarboxylative Allylation of α‐Trifluoromethyl β‐Keto Esters

ChemInform Abstract: Formation of Quaternary Carbon Center with a Trifluoromethyl Group Using a Pd‐Catalyzed Allylation Reaction.

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