One‐Pot Regioselective γ‐Trifluoromethylthiolation and γ‐Methylthiolation of Enals

Banoun, Camille; Henault, Killian; Magnier, Emmanuel; Dagousset, Guillaume

doi:10.1002/ejoc.202400119

Eur J Org Chem

2024

DOI: 10.1002/ejoc.202400119

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One‐Pot Regioselective γ‐Trifluoromethylthiolation and γ‐Methylthiolation of Enals

Camille Banoun,

Killian Henault,

Emmanuel Magnier

et al.

Abstract: We describe herein the direct electrophilic γ‐trifluoromethylthiolation and γ‐methylthiolation of enals, via the in situ formation of the corresponding silyl dienol ether. This one‐pot process is carried out under simple and mild reaction conditions and is compatible with a variety of functional groups.

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Cited by 2 publications

References 37 publications

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Photocatalyzed One‐Pot Selective Synthesis of γ‐(per)fluoroalkenylated α,β‐Unsaturated Carbonyl Compounds

Briand,

Magnier,

Anselmi

et al. 2024

Adv Synth Catal

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We report herein a general one‐pot perfluoroalkylation/dehydrohalogenation protocol for the selective perfluoroalkenylation of silyl dienol ethers in their γ position. Importantly, this methodology is applicable to the synthesis of a wide range of γ‐perfluoroalkenylated enals, enones and α,β‐unsaturated amides. Various perfluoroalkenyl moieties could be efficiently introduced, with an important impact on the E/Z diatereoselectivity of the newly formed fluorinated double bond.

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Photocatalyzed One‐Pot Selective Synthesis of γ‐(per)fluoroalkenylated α,β‐Unsaturated Carbonyl Compounds

Briand,

Magnier,

Anselmi

et al. 2024

Adv Synth Catal

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Synthesis of Chromene Derivatives from α,β‐Unsaturated Aldehydes: A Review

Vchislo,

Verochkina

2024

Eur J Org Chem

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Chromene derivatives are important oxygen heterocycles, which are met in numerous natural products, pharmaceuticals, and organic functional materials. This review survey the achievements in the synthesis of chromenes derivatives from α,β‐unsaturated aldehydes. Particular attention is paid to the use of catalytic systems, synthetic advantages and mechanistic aspects of the reactions. The works published over the past 15 years are covered.

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One‐Pot Regioselective γ‐Trifluoromethylthiolation and γ‐Methylthiolation of Enals

Cited by 2 publications

References 37 publications

Photocatalyzed One‐Pot Selective Synthesis of γ‐(per)fluoroalkenylated α,β‐Unsaturated Carbonyl Compounds

Photocatalyzed One‐Pot Selective Synthesis of γ‐(per)fluoroalkenylated α,β‐Unsaturated Carbonyl Compounds

Synthesis of Chromene Derivatives from α,β‐Unsaturated Aldehydes: A Review

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