NHC-Catalyzed Regioselective Intramolecular Radical Cyclization Reaction for the Synthesis of Benzazepine Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6072 - 6076

Published: Aug. 8, 2023

A novel and efficient strategy for the synthesis of a series structurally interesting benzazepine derivatives via an N-heterocyclic carbene-catalyzed regioselective intramolecular radical cyclization has been developed. This protocol features good regioselectivity, functional-group compatibility, wide substrate scope, providing transition-metal- oxidant-free pathway to access seven-membered rings under mild reaction conditions. Additionally, further transformation benzazepines large-scale experiment were also conducted.

Language: Английский

---

Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines

Organic Letters, Journal Year: 2022, Volume and Issue: 24(50), P. 9243 - 9247

Published: Dec. 14, 2022

A number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed insertion into biaryl isonitriles, thus leading to the rapid assembly a variety diversely functionalized 6-cyanoalkyl phenanthridines. preliminary mechanism study revealed that single-electron transfer radical process was possibly involved.

Language: Английский

---

Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh₃ Dual Catalysis

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9186 - 9190

Published: Dec. 15, 2023

The photoredox/PPh3-mediated cyclization of 2-isocyanobiaryls has been developed. A substantial range functional-group-rich phenanthridine derivatives were synthesized at room temperature in a highly selective and atom-economic manner. Mechanistic studies suggested that the process is probably mediated both by Ph3P radical cation with key 1,2-hydride transfer hydrogen atom generated through O–H bond homolytic cleavage Ph3P–OH intermediate.

Language: Английский

---

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

ChemistryOpen, Journal Year: 2024, Volume and Issue: unknown

Published: July 11, 2024

Abstract This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. compound a carbon has been used primarily only as radical initiator in atom transfer polymerization (ATRP) reactions. However, recent development photo‐radical reactions (around 2010), research on use alkyl precursors became popular 2012). As more examples were reported, studied not radicals but also for their applications organometallic and ionic That is, act nucleophiles well electrophiles. The carbonyl group is attractive because it allows skeleton to be converted after reaction, being applied total synthesis. In our survey until 2022, can perform full range necessary synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific asymmetric α‐Bromocarbonyl have created new trend alkylation, which then had limited reaction patterns focuses how chemistry.

Language: Английский

---

Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8149 - 8153

Published: Sept. 16, 2024

Indole and quinoline structures are present in numerous biologically active molecules, making the synthesis of their glycosylation products a subject extensive research interest drug development. Here, we report photoredox strategy for

Language: Английский

---

Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines

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

Published: Jan. 1, 2025

A photochemical radical cascade cyclization reaction of isocyanides with α-carbonyl bromides under mild conditions is disclosed for accessing 1,4-dibenzodiazepines, demonstrating good tolerance towards various functional groups.

Language: Английский

---

Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100124 - 100124

Published: Feb. 1, 2025

Language: Английский

---

Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines

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

Published: March 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Language: Английский

---

1,2-Aminoalkylacylation of styrenes by cooperative NHC/photoredox dual catalysis

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 9

Published: April 3, 2025

Language: Английский

---

The cascade annulation approach to quinoxalines by radical NHC catalysis

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Language: Английский

---