Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

---

Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2398 - 2402

Published: March 18, 2024

Herein, we introduce a tetralone-mediated photocyclization method of N-arylacrylamides. The protocol proceeds smoothly to deliver diverse set 3,4-dihydroquinolinones in moderate good yields with excellent functional group compatibility and readily allows for late-stage modifications number complex drug molecules. Mechanistic studies reveal that the present systems ultraviolet light irradiation enable cyclization via energy transfer exclusive 1,3-hydrogen shift.

Language: Английский

---

Selective Reduction of Triple Bond via Proton-Coupled Electron Transfer for the Synthesis of α,β-Unsaturated γ-Lactams

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3982 - 3986

Published: May 1, 2024

Described herein is the development of a visible-light-induced photoredox 1,6-enyne reductive cyclization via selective reduction triple bond instead an activated double bond. The radical cyclization/carbon═carbon cleavage provided straightforward route to structurally valuable

Language: Английский

---

p-Diarylboryl Halothiophenols as Multifunctional Catalysts via Photoactive Intramolecular Frustrated Lewis Pairs

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 20425 - 20431

Published: July 8, 2024

p-Diarylboryl halothiophenols are developed and unequivocally characterized. Their photophysical properties catalytic performance unveiled by experimental theoretical investigations. This novel class of triarylboranes behaves as a Brønsted acid to generate the corresponding borylthiophenolate that can absorb visible light undergo intramolecular charge transfer form radical pair consisting boron anion thiyl radical, which acts single-electron reductant while engaging in hydrogen atom regenerate parent borylthiophenol. The synthetic relevance this mode action is demonstrated establishment unique catalysis integrates three different yet tunable functions single cycle, thereby allowing borylthiophenols solely promote assembly sterically congested 1,2-diols 1,2-aminoalcohol derivatives via radical–radical cross-coupling.

Language: Английский

---

Silver-Catalyzed Cascade Radical Bicyclization Reaction: An Atom- and Step-Economical Strategy Accessing γ-Lactam Containing Isoquinolinediones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15428 - 15436

Published: Oct. 21, 2023

An efficient and convenient method for the cascade radical bicyclization of N-phenyl-4-pentenamides with N-methyl-N-methacryloylbenzamides under silver-catalyzed conditions is described. Based on this newly developed strategy, a variety valuable γ-lactam containing isoquinolinediones can be effectively synthesized in one step within 0.5 h, during which two C-C bonds, C-N bond, new N-heterocycles were formed concurrently. With N-aryl allyl carbamates, similar 2-oxazolidinone substituted isoquinolinedione compounds likewise produced. The approach demonstrates wide functional group compatibility, high step- atom-economy, ability to scaled up gram quantities satisfactory yield. It marks first instance introducing γ-lactams into isoquinoline-1,3(2H,4H)-diones construct linked hybrid drug-like molecules, thereby making strategy highly attractive drug discovery.

Language: Английский

---

Cation-π-interaction-facilitated, self-photocatalyzed and regioselective perfluoroalkylation of 3-aza-1,5-dienes

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 547, P. 113360 - 113360

Published: July 7, 2023

Language: Английский

---

Photocatalytic Proton-Coupled Electron Transfer Enabled Radical Cyclization for Isoquinoline-1,3-diones Synthesis

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5060 - 5068

Published: March 25, 2024

Radical cyclization has been demonstrated to be an efficient method access functionalized heterocycles from easily accessible raw materials. Described herein is the development of a photocatalytic proton-coupled electron transfer (PCET) strategy for synthesis isoquinoline-1,3-diones using readily prepared naphthalimide (NI)-based organic photocatalysts. The process features free metal-complex photocatalysts, acids, and mild reaction conditions. This radical protocol broad substrate scope can effectively applied variety medicinally relevant substrates. Furthermore, control experiments were conducted elucidate mechanism this visible light-induced methodology.

Language: Английский

---

Photoinduced Single‐Electron Reduction of Alkenes.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(2)

Published: Nov. 9, 2023

Abstract Alkenes serve as versatile building blocks in organic synthesis. However, the challenge of achieving single‐electron reduction alkenes persists. In recent years, photocatalysis has emerged a promising and efficient tool for accomplishing alkenes. Given potential benefits that can be derived from photoinduced alkenes, including development potent catalytic systems to enable diverse alkene difunctionalization reactions, it is necessary provide conceptual understanding this emerging field. Hence, we present an overview current synthetic techniques

Language: Английский

---