Functionalization of Boranes through Thiol/Oxygen Catalysis† DOI Creative Commons

Hongyi Tao,

Hairong Lyu

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(22), P. 2804 - 2810

Published: July 17, 2024

Comprehensive Summary A greener and more convenient alternative to traditional methods for the generation of thiyl radical as hydrogen atom transfer (HAT) catalyst is developed, using molecular oxygen oxidize thiol without need chemical initiators or light irradiation. The thiol/oxygen catalysis enables selective efficient difunctionalization borane.

Language: Английский

Regioselective Homolytic C2–H Borylation of Unprotected Adenosine and Adenine Derivatives via Minisci Reaction DOI

Yangyan Li,

Yutong Zhou,

Dazhi Zhou

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(31), P. 21428 - 21441

Published: July 25, 2024

A Minisci-type borylation of unprotected adenosine, adenine nucleotide, and adenosine analogues was successfully achieved through photocatalysis or thermal activation. Despite the challenges posed by presence two potential reactive sites (C

Language: Английский

Citations

3
Advances in Pyridine C – H Functionalizations: Beyond C2 Selectivity DOI
Sachin Balaso Mohite, Yafia Kousin Mirza, Partha Sarathi Bera

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(2)

Published: Nov. 28, 2024

The pyridine core is a crucial component in numerous FDA-approved drugs and Environmental Protection Agency (EPA) regulated agrochemicals. It also plays significant role ligands for transition metals, alkaloids, catalysts, various organic materials with diverse properties, making it one of the most important structural frameworks. However, despite its significance, direct selective functionalization still relatively underdeveloped due to electron-deficient nature strong coordinating ability nitrogen. Among variety synthetic transformation, C-H bond straightforward atom economical approach it's advantageous late-stage containing drugs. In recent years, innovative strategies regioselective pyridines azines have emerged, offering benefits such as high regioselectivity, mild conditions, enabling transformations that were challenging traditional methods. This review emphasizes latest advancements meta para-C-H through approaches, including phosphonium salts, photocatalytic methods, temporary de-aromatization, Minisci-type reactions, metal-catalyzed activation techniques. We discuss advantages limitations these current methods aim inspire further progress this field.

Language: Английский

Citations

3
Spirobipyridine Ligands as a Unique Platform for Substrate Recognition and Reaction Control through Noncovalent Interactions DOI
Sobi Asako, Laurean Ilies

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6372 - 6379

Published: April 4, 2025

Language: Английский

Citations

0
Photoinduced C–H Functionalization of Pyridines with N-Functionalized Pyridinium Salts DOI
H. L. Ju, Sungwoo Hong

Topics in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Photocatalyst‐ and Transition Metal‐Free Light‐Induced Borylation Reactions DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(21)

Published: Sept. 25, 2023

The increasing global warming concerns have propelled a surge in the demand for sustainable energy sources within domain of synthetic organic chemistry. A particularly prominent area research has been development mild strategies generating heterocyclic compounds. Heterocyclic compounds containing boron notably risen to prominence as pivotal reagents myriad transformations, showcasing their wide-ranging applicability. This comprehensive review is aimed at collecting literature pertaining borylation reactions induced by light, specifically focusing on photocatalyst-free and transition metal-free methodologies. central emphasis delving into selective mechanistic investigations. amalgamation analysis these insights elucidate substantial potential inherent eco-friendly approaches synthesizing compounds, thus propelling landscape

Language: Английский

Citations

9
Photoredox-Catalyzed Tandem Cyclization of Enaminones with N-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones DOI
Wenyu Hu, Xiaoqiong Diao, Jinwei Yuan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 644 - 655

Published: Dec. 13, 2023

A photoredox-catalyzed intermolecular tandem sulfonamination/cyclization of enaminones was realized by using N-aminopyridinium salts as the sulfonaminated reagents without transition-metal catalysts or bases. The reaction exhibits a broad scope and good functional group tolerance, yields, regioselectivity. Preliminary mechanistic studies support radical property involvement N-centered intermediates.

Language: Английский

Citations

9
Enhanced Efficiency of Amide‐Substituted Quinuclidine‐Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins† DOI
Yang Xiao,

Mengsi Ma,

Meichen Xu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 10, 2024

Comprehensive Summary An amide‐substituted quinuclidine‐borane has been identified as a more efficient hydridic hydrogen atom transfer (HAT) catalyst for the hydroalkylation of unactivated olefins under visible‐light irradiation. 1 H NMR titration experiments reveal that amide moiety forms stronger bonds with carbonyl substrates, thereby improving reaction yields. Furthermore, it was found yields correlate well association constant between and substrate. A scale‐up using continuous‐flow photoreactor also demonstrated.

Language: Английский

Citations

2
Recent Advances in Methodologies for Radical‐Mechanistic Borylation† DOI

Chang Lian,

Jianning Zhang, Di Qiu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Comprehensive Summary We reviewed works on radical borylation reactions since 2020 from two aspects. 1. Borylation alkyl or aryl radicals : This approach involves the generation of various precursors such as halides and carboxylic acids, followed by their reaction with diboron reagents to form boron esters. 2. boron‐centered generating radicals, which then react substrates achieve borylation. Key Scientists

Language: Английский

Citations

2
Recent Advances in Borylation via Electron Donor–Acceptor Complex Photoactivation DOI

Guanwen Hu,

Zhiyong Wang,

Xinmou Wang

et al.

ChemPhotoChem, Journal Year: 2023, Volume and Issue: 7(11)

Published: July 19, 2023

Abstract Photoinduced borylation is becoming a fascinating and growing research field in synthetic chemistry. On the other hand, electron donor–acceptor (EDA) complex photoactivation has emerged as an alternative strategy to generate active open‐shell species without need for photosensitizers. Suitable organoboron compounds can serve donor or acceptor form corresponding complexes, which then undergo photoinduced intracomplex single transfer (SET) carbon‐ boron‐centered radicals construction of new C−B bonds. In this Concept paper, we review recent advances via EDA surveying relevant literature until December 2022.

Language: Английский

Citations

4
An electron-donor–acceptor complex between two intermediates enables a N–N bond cleavage cascade process to access 2,3-difunctionalized pyridines DOI Creative Commons
Yazhou Liu, Yu Chen, Amu Wang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(4), P. 2280 - 2289

Published: Jan. 1, 2024

A visible-light-enabled catalyst-free [3 + 2] cycloaddition/N–N bond cleavage/intramolecular C–N formation cascade process to access 2,3-difunctionalized pyridines was developed.

Language: Английский

Citations

1