Highly selective γ-alkoxylation, γ-amination and γ-alkylation of unbiased enals by means of photoredox catalysis

Banoun, Camille; Bourdreux, Flavien; Dagousset, Guillaume

doi:10.1039/d2cc05749b

Cited by 5 publications

(2 citation statements)

References 35 publications

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“…Pleasingly, by changing the photocatalyst from Ru(bpy)3(PF6)2 (used for alkoxylation of ketones and amides, Scheme 19) to Ir(ppy)3, various -alkoxylated enals were obtained in good yields, with full -regioselectivity. 38 Template for SYNLETT Thieme Scheme 21 Regioselective -alkoxylation of enals from the corresponding silyl dienol ethers…”

Section: Reactions Involving Alkoxy Radicalsmentioning

confidence: 99%

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Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation

Banoun

Magnier

Dagousset

2023

Synlett

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Section: Reactions Involving Alkoxy Radicalsmentioning

confidence: 99%

“…Pleasingly, by changing the photocatalyst from Ru(bpy) 3 (PF 6 ) 2 (used for α-alkoxylation of ketones and amides, Scheme 19 ) to Ir(ppy) 3 , various γ-alkoxylated enals 57 were obtained in good yields, with full γ-regioselectivity. 38…”

Section: Reactions Involving Alkoxy Radicalsmentioning

confidence: 99%

Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation

Banoun

Magnier

Dagousset

2023

Synlett

Self Cite

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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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Photocatalytic α‐Difluoroalkoxyketones Synthesis via Radical Intermolecular Alkoxylation of Difluoroenol Silyl Ethers

Paut,

Baldon,

Anselmi

et al. 2024

Adv Synth Catal

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Abstract. We present a new metal‐free photocatalytic approach for the synthesis of difluoroalkoxylated ketones. This strategy involves the generation of alkoxyl radicals from pyridinium salts upon the activity of a catalytic electron‐donor‐acceptor (EDA) complex. This mild process tolerates several functional groups and can be scaled up to gram scale. Diverse products manipulations accounts for the versatility of the obtained fluorinated products, highlighting the synthetic usefulness of this method.

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Highly selective γ-alkoxylation, γ-amination and γ-alkylation of unbiased enals by means of photoredox catalysis

Abstract: We report herein a general and highly selective γ-functionalization protocol under visible light irradiation. This mild radical approach enables to expand the scope of application to unbiased enals and to...

Cited by 5 publications

References 35 publications

Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation

Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation

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

Photocatalytic α‐Difluoroalkoxyketones Synthesis via Radical Intermolecular Alkoxylation of Difluoroenol Silyl Ethers

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