Formate Salts: The Rediscovery of Their Radical Reaction under Light Irradiation Opens New Avenues in Organic Synthesis

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4274 - 4293

Published: Aug. 17, 2024

Abstract Formates are abundantly available and inexpensive commodity chemical, widely used in laboratory industrial organic synthesis. promising hydrogen carrier green C1 source, have also been a subject of research as SET reductants recent years. Compared to the toxic flammable gas carbon monoxide, which serves formates easier handle, store, transport, more environmentally friendly. Therefore, studies radical reactions, formate is not only an ideal source carbonyl, great significance synthesize carboxyl compounds with various structures, but reductant for editing molecules either scientific or production. The activation conversion formate, reductant, very challenging hot field

Language: Английский

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Synthetic application of oxalate salts for visible-light-induced radical transformations

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111224 - 111224

Published: April 1, 2025

Language: Английский

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Alkene Carboxy-Alkylation via CO₂^•–

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(51), P. 35035 - 35042

Published: Dec. 12, 2024

Herein, we introduce a new platform for alkene carboxy-alkylation. This reaction is designed around CO

Language: Английский

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Visible-Light-Driven Carboxylative 1,2-Difunctionalization of C═C Bonds with Tetrabutylammonium Oxalate

ACS Central Science, Journal Year: 2024, Volume and Issue: 11(1), P. 46 - 56

Published: Nov. 15, 2024

Herein, we report a visible-light-induced charge-transfer-complex-enabled dicarboxylation and deuterocarboxylation of C═C bonds with oxalate as masked CO2 source under catalyst-free conditions. In this reaction, disclosed the first example that tetrabutylammonium could be able to aggregate aryl substrates via π–cation interactions form charge transfer complexes, which subsequently triggers single electron from oxalic dianion ammonium countercation irradiation 450 nm bule LEDs, releasing radical anions. Diverse alkenes, dienes, trienes, indoles, including challenging trisubstituted olefins, underwent anti-Markovnikov high selectivity access valuable 1,2- 1,4-dicarboxylic acids well indoline-derived diacids β-deuterocarboxylic mild The in situ generated CO2•– molecules anions both add bond without assistance any photocatalyst or additives, made reaction sustainable, clean, efficient.

Language: Английский

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Trans-selective carboxylative cyclization of 1,6-dienes using the CO2 radical anion

Chemistry Letters, Journal Year: 2024, Volume and Issue: 53(8)

Published: July 26, 2024

Abstract The reactivity of the carbon dioxide radical anion (CO2•−) toward alkenes has garnered remarkable attention owing to its potential synthesize valuable organic compounds. Herein, we report reactions between CO2•− and 1,6-dienes, yielding 5-membered lactam derivatives via highly trans-selective 5-exo-trig cyclization. Both carboxylative cyclization hydrocyclization occur with up 74% combined yield. Computational studies show that transition state during favors trans-configuration over cis-configuration. This work offers new insights into synthesis N-heterocycles.

Language: Английский

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Photoredox-Catalyst-Free Carboxylation of Unactivated Alkenes in DMSO: Synthesis of Polycyclic Indole Derivatives and Aliphatic Acids

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 6, 2024

A new method for the carboxylation of unactivated alkenes using CO

Language: Английский

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