Photoredox-Catalyzed Defluorinative Carboxylation of gem-Difluorostyrenes with Formate Salt

Organic Letters, Год журнала: 2024, Номер 26(4), С. 883 - 888

Опубликована: Янв. 22, 2024

Herein, we present a transition-metal-free, easy handling protocol for regioselective carboxylation of gem-difluorostyrenes with sodium formate as the C1 source. 30 examples α-fluoracrylates were obtained in yields to 80% under these conditions. A defluorinative monofluorovinyl intermediate and consecutive photoinduced electron transfer mechanism proposed after investigation.

Язык: Английский

---

Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 26, 2025

A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, (NH4)2CO3 through the cleavage five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this features mild conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification complex molecules, scalability, versatile synthetic transformations resulting heterocyclic compounds.

Язык: Английский

---

Stereoselective hydrodefluorination of CF₃-substituted alkenes and gem-difluoroalkenes by H⁻

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1388 - 1394

Опубликована: Янв. 1, 2024

Zn-catalyzed stereoselective hydrodefluorination of CF 3 -substituted alkenes, gem -difluoroalkenes and polyfluoroarenes by hydride ion addition has been realized through controlled C(sp )–F and/or 2 bonds cleavage.

Язык: Английский

---

Formate and CO₂ Enable Reductive Carboxylation of Imines: Synthesis of Unnatural α-Amino Acids

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 9750 - 9754

Опубликована: Июнь 28, 2024

Herein, a photocatalytic umpolung strategy for reductive carboxylation of imines the synthesis α-amino acids was disclosed. Carbon dioxide radical anion (CO

Язык: Английский

---

Photocatalytic deuterocarboxylation of alkynes with oxalate

Chemical Science, Год журнала: 2024, Номер 15(32), С. 13041 - 13048

Опубликована: Янв. 1, 2024

Herein, a catalytic photoredox-neutral strategy for alkyne deuterocarboxylation with tetrabutylammonium oxalate as the carbonyl source and D

Язык: Английский

---

Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate

ACS Catalysis, Год журнала: 2024, Номер 14(16), С. 11967 - 11973

Опубликована: Июль 26, 2024

Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source reductant well promoter is described. Neither pre-established CO2 atmosphere nor external electron donors are required TBAO crucial transformation. Various primary, secondary, tertiary could be smoothly converted to corresponding aryl acetic acids, which core structures diverse pharmaceutical drugs.

Язык: Английский

---

Visible-Light-Promoted Cascade Carboxylation/Arylation of Unactivated Alkenes with CO₂ for the Synthesis of Carboxylated Indole-Fused Heterocycles

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6341 - 6346

Опубликована: Июль 18, 2024

Described here is a visible-light-promoted cascade carboxylation/arylation of indole-tethered unactivated alkenes with CO

Язык: Английский

---

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

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4274 - 4293

Опубликована: Авг. 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

Язык: Английский

---

Photoinduced Dehalocyclization to Access Oxindoles Using Formate as a Reductant

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(11), С. 1203 - 1208

Опубликована: Фев. 6, 2024

Comprehensive Summary Herein, we report an efficient and practical protocol for the photoinduced dehalocyclization of ortho ‐halophenylacrylamides with formate by engagement a CO 2 radical anion to access substituted oxindoles. This method proceeds smoothly under mild conditions exhibits wide range substrate as well remarkable functional group compatibility.

Язык: Английский

---

Mild [3 + 3] Annulation of (Trifluoromethyl)alkenes with Thioureas Enabled by Chemoselective Defluorinative Amination: Synthesis of 6-Fluoro-3,4-dihydropyrimidine-2(1H)-thiones

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1538 - 1548

Опубликована: Янв. 21, 2025

The chemoselective defluorinative [3 + 3] annulation of (trifluoromethyl)alkenes with thioureas is reported. This protocol affords various attractive 6-fluoro-3,4-dihydropyrimidine-2(1H)-thiones in high yields, features transition-metal free, mild conditions, efficient, operationally simple and gram-scalable, tolerates diverse useful functional groups.

Язык: Английский

---