Carbene-catalyzed [3 + 2 + 1] annulation via C–N radical coupling of iminyl radicals and ketyl radicals DOI

Wenchang Li,

Peng Zhou, Qing Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(18), P. 3784 - 3788

Published: Jan. 1, 2023

An NHC-catalyzed [3 + 2 1] annulation of vinyl azides, aldehydes, and Togni’s reagents was reported. The cascade involves SET redox transformation, denitrogenated radical migration, C–N coupling, defluorinated cyclization.

Language: Английский

A crystalline doubly oxidized carbene DOI
Ying Kai Loh, Mohand Melaïmi, Milan Gembický

et al.

Nature, Journal Year: 2023, Volume and Issue: 623(7985), P. 66 - 70

Published: Sept. 20, 2023

Language: Английский

Citations

28
1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants DOI
Mehdi Abdellaoui, Kai Oppel, Adam Vianna

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(5), P. 2933 - 2938

Published: Jan. 22, 2024

Most of the known single-electron reductants are either metal based reagents, used in a stoichiometric amount, or combination an organic species and photocatalyst. Here we report that 1

Language: Английский

Citations

13
Visible-Light-Induced Redox-Neutral Difunctionalization of Alkenes and Alkynes DOI
Susmita Mondal, Sumit Ghosh, Alakananda Hajra

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9659 - 9691

Published: Jan. 1, 2024

The twelve principles of green chemistry illuminate the pathway in direction sustainable and eco-friendly synthesis, marking a fundamental shift synthetic organic paradigms. In this realm, harnessing power visible light for difunctionalization various skeletons without employing any external oxidant or reductant, specifically termed as redox-neutral difunctionalization, has attracted tremendous interest from chemists due to its low cost, easy availability environmentally friendly nature contrast traditional metal-catalyzed difunctionalizations. This review presents an overview recent updates on visible-light-induced reactions with literature coverage up May 2024.

Language: Английский

Citations

12
Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures DOI
Han Liu, Lei Wang, Jin‐Tao Yu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

Citations

23
NHC-Catalyzed Regioselective Intramolecular Radical Cyclization Reaction for the Synthesis of Benzazepine Derivatives DOI
Nengneng Zhou,

Fangli Zhao,

Lei Wang

et al.

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

Citations

12
Redox-Neutral Cyclization of 2-Isocyanobiaryls through Photoredox/PPh3 Dual Catalysis DOI
Xiaoting Wu, Pu Chen,

Mengran Gan

et al.

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

Citations

11
α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source DOI Creative Commons
Takashi Nishikata

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

Citations

4
Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines DOI

Qianrong Li,

Cong‐Ying Zhou,

Chengming Wang

et al.

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

Citations

17
Visible-Light-Initiated Sequential Trifluoromethylation/Remote C(sp3)–H Alkynylation of Vinyl Azides by Radical Relay DOI
Zirui Chen,

Yunnan Duan,

Shitao Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4687 - 4693

Published: March 13, 2023

A visible-light-initiated trifluoromethylation/remote aliphatic C-H alkynylation of α-alkyl-substituted vinyl azides using acetylenic triflones as both the trifluoromethyl and alkyne donors is described. The reaction occurred under environmentally benign radical initiator-free conditions, affording γ-alkynylated ketone derivatives with a broad scope substituents. Mechanistic studies suggested that initiated via triplet-triplet energy transfer between 4CzIPN catalyst triflone, followed by fragmentation to generate an alkynyl radical.

Language: Английский

Citations

10
Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation DOI Creative Commons

Tinglan Liu,

Pan Yue, Chengming Wang

et al.

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

Published: Feb. 1, 2025

Language: Английский

Citations

0