Photocatalytic [3+2] Cycloaddition of Alkyl/aryl Iodides and Internal Alkynes by Merging Halogen and Hydrogen Atom Transfer DOI Creative Commons
Zhenyu Gu,

Rong Jia,

Tianqing Zeng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(19), P. 2329 - 2334

Published: May 22, 2024

Comprehensive Summary A visible light photocatalytic [3+2] cycloaddition of alkynes with readily accessible organic iodides as the C3 synthon is developed herein. By merging halogen atom transfer (XAT) and hydrogen (HAT), alkyl/aryl serve a formal diradical precursor add across C‐C triple bonds to deliver number functionalized cyclopentanes in moderate high yields exceptional regio‐ diastereoselectivity. reductive radical‐polar crossover mechanism, involving cascade XAT, radical addition, 1,5‐HAT, polar effect‐promoted 5‐endo annulation, single electron (SET) reduction, protonation, may account for this unprecedented dehalogenative cycloaddition. This work not only expands repertoire traditional RATC methodology, but also provides robust platform expedient assembly cyclopentanes, valuable structural motif realms medicinal chemistry material sciences.

Language: Английский

Recent advances in hydrogen atom transfer induced C(sp3)–H functionalizations initiated by radical addition to alkynes DOI
Yulu Zhou, Zhenyu Gu,

Yuwei Hong

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(4), P. 1232 - 1250

Published: Dec. 28, 2023

Recent advances in HAT-induced C(sp 3 )–H functionalizations triggered by radical addition to alkynes, including 5- exo-trig , endo-trig 4- and 6- cyclization cascades, intermolecular functionalizations, are summarized.

Language: Английский

Citations

15
Advancement in Synthetic Strategies of Phosphorus Heterocycles: Recent Progress from Synthesis to Emerging Class of Optoelectronic Materials DOI

Deepika Thakur,

Sushmita Sushmita,

Shivam A. Meena

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: 24(8)

Published: Aug. 1, 2024

Organophosphorus heterocycles have long been acknowledged for their significant potential across diverse fields, including catalysis, material science, and drug development. Incorporating phosphorus functionalities into organic compounds offers a means to effectively tailor medicinal properties, augment biological responses, enhance selectivity bioavailability. The distinctive physical photoelectric characteristics of phosphorus-containing conjugated garnered considerable interest as promising materials optoelectronics. These find extensive utility in various applications such light-emitting diodes, photovoltaic cells, phosphole-based fluorophores, semiconductors.

Language: Английский

Citations

6
Recent Advances in Visible Light Induced Radical 1,2-Functionalization of Alkynes DOI

Kangkui Li,

Xianyang Long,

Yue Huang

et al.

Acta Chimica Sinica, Journal Year: 2024, Volume and Issue: 82(6), P. 658 - 658

Published: Jan. 1, 2024

Language: Английский

Citations

4
Advanced green synthesis: Solvent-free and catalyst-free reaction DOI Creative Commons
Mengyao Li,

Ao Gu,

Jiatong Li

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

Citations

4
Research on Alkyne Carbon Cyclization Reactions Based on Intermolecular Radical Addition/Translocation/Cyclization (RATC) Strategy DOI

岚茜 周

Journal of Organic Chemistry Research, Journal Year: 2025, Volume and Issue: 13(01), P. 1 - 12

Published: Jan. 1, 2025

Language: Английский

Citations

0
Photocatalytic Cyclization of 2-Phosphinobiaryls to Trivalent Dibenzophospholes DOI
Yusuke Masuda, Yu Harabuchi, Yuki I. Kawamura

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6514 - 6524

Published: April 7, 2025

Language: Английский

Citations

0
Photocatalytic Phosphine-Mediated Deoxygenative [3 + 2] Cycloaddition of α,β-Unsaturated Carbonyls and Alkenes DOI

Jiayan Qiu,

Xuemei Zhang,

Hanliang Zheng

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

Tertiary phosphine is a powerful nucleophile that enables numerous synthetically important reactions. However, the exclusive reliance on two-electron pathway has restricted development of chemistry. We report here visible light photocatalytic phosphine-mediated deoxygenative [3 + 2] cycloaddition α,β-unsaturated carbonyls and activated alkenes, providing facile access to polysubstituted cyclopentenes from readily accessible starting materials in promising yields with good substrate scope. Mechanistic investigations corroborate transient involvement radical cation consequent α-addition (α electron-withdrawing groups) C-C double bonds due inherent electrophilicity cation, as opposed traditional nucleophilic β-addition phosphine. The ensuing single electron transfer reduction, Michael addition, 1,4-proton cascade furnish phosphorus ylide, which undergoes an intramolecular Wittig reaction finish construction cyclopentenes. This work demonstrates tertiary can serve convenient reagent for carbonyl deoxygenation act traceless directing group controllable cross-coupling two distinct new avenues expand frontiers chemistry synthetic

Language: Английский

Citations

0
Cobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxides via C–H activation and formal phosphoryl migration DOI Creative Commons
Shengbo Xu,

Ruijie Mi,

Guangfan Zheng

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 6012 - 6021

Published: Jan. 1, 2024

A highly stereo- and chemoselective intermolecular coupling of diverse heterocycles with dialkynylphosphine oxides has been realized

Language: Английский

Citations

2
Photocatalytic [3+2] Cycloaddition of Alkyl/aryl Iodides and Internal Alkynes by Merging Halogen and Hydrogen Atom Transfer DOI Creative Commons
Zhenyu Gu,

Rong Jia,

Tianqing Zeng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(19), P. 2329 - 2334

Published: May 22, 2024

Comprehensive Summary A visible light photocatalytic [3+2] cycloaddition of alkynes with readily accessible organic iodides as the C3 synthon is developed herein. By merging halogen atom transfer (XAT) and hydrogen (HAT), alkyl/aryl serve a formal diradical precursor add across C‐C triple bonds to deliver number functionalized cyclopentanes in moderate high yields exceptional regio‐ diastereoselectivity. reductive radical‐polar crossover mechanism, involving cascade XAT, radical addition, 1,5‐HAT, polar effect‐promoted 5‐endo annulation, single electron (SET) reduction, protonation, may account for this unprecedented dehalogenative cycloaddition. This work not only expands repertoire traditional RATC methodology, but also provides robust platform expedient assembly cyclopentanes, valuable structural motif realms medicinal chemistry material sciences.

Language: Английский

Citations

2