Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

Carboxylic acids are bench-stable and readily available chemical feedstocks that function as optimal fundamental synthetic platforms for the construction of C(sp3)–C(sp3) bonds via decarboxylation processes. We present a novel practical protocol decarboxylative alkylation Morita–Baylis–Hillman acetates with various carboxylic photoinduced iron-mediated ligand-to-metal charge transfer (LMCT) process under redox-neutral conditions. This method exhibits remarkable tolerance to wide array acids, including primary, secondary, tertiary obviating requirement preactivated radical precursors. The preliminary mechanistic analyses indicate pathway is involved in this catalytic transformation.

Language: Английский

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Direct C–H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2777 - 2781

Published: Feb. 5, 2024

2,1,3-Benzothiadiazole is widely used as a privileged scaffold in pharmaceuticals and organic functional materials. Nonetheless, many current methods for the functionalization of 2,1,3-benzothiadiazole rely on preactivation, transition metal catalysts/promoters, or an elevated reaction temperature. Herein we disclose transition-metal-free visible-light-induced photocatalytic method direct C–H alkylation using readily accessible carboxylic acid derivatives, i.e., N-hydroxyphthalimide esters (NHPEs), alkylating reagents under room This mild scalable highlighted by late-stage installation benzothiadiazole drugs natural products.

Language: Английский

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Visible light-mediated decarboxylative allylic alkylation of Morita–Baylis–Hillman acetates with unactivated aliphatic acids

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Herein, a visible light-induced and metal-free strategy for the direct decarboxylative allylic alkylation of Morita–Baylis–Hillman acetates with aliphatic acids under redox-neutral conditions has been developed.

Language: Английский

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Photoredox/Nickel-Catalyzed Diastereoselective Allylation of Aldehydes with Morita–Baylis–Hillman Adducts

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 8303 - 8316

Published: May 2, 2025

Language: Английский

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Electrochemical Stereoselective Synthesis of (Z)‐Allyl Aryl Selenides and Sulfides from Baylis‐Hillman Acetates

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1152 - 1157

Published: Jan. 9, 2024

Abstract This research presents a method for the oxidative selenylation and thiolylation of Morita‐Baylis‐Hillman adducts through constant‐current electrolysis in an undivided cell at room temperature. The reaction enables direct production trisubstituted ( Z )‐allyl aryl selenides sulfides with yields 27–98%. A wide variety different functionalities are well tolerated under these conditions. strategy could be carried out on gram scale several synthetic transformations were accomplished construction other allyl selenide derivatives. Control experiments mechanistic studies indicate radical or ionic addition pathway this electrochemical transformation.

Language: Английский

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