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

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(19), С. 2329 - 2334

Опубликована: Май 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.

Язык: 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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(4), С. 1232 - 1250

Опубликована: Дек. 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.

Язык: Английский

Процитировано

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

и другие.

The Chemical Record, Год журнала: 2024, Номер 24(8)

Опубликована: Авг. 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.

Язык: Английский

Процитировано

6

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

Kangkui Li,

Xianyang Long,

Yue Huang

и другие.

Acta Chimica Sinica, Год журнала: 2024, Номер 82(6), С. 658 - 658

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

4

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

Ao Gu,

Jiatong Li

и другие.

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 1, 2024

Язык: Английский

Процитировано

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, Год журнала: 2025, Номер 13(01), С. 1 - 12

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

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

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6514 - 6524

Опубликована: Апрель 7, 2025

Язык: Английский

Процитировано

0

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

Jiayan Qiu,

Xuemei Zhang,

Hanliang Zheng

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Май 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

Язык: Английский

Процитировано

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

и другие.

Chemical Science, Год журнала: 2024, Номер 15(16), С. 6012 - 6021

Опубликована: Янв. 1, 2024

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

Язык: Английский

Процитировано

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

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(19), С. 2329 - 2334

Опубликована: Май 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.

Язык: Английский

Процитировано

2