C(sp3)‐F Bond Activation by Lewis Base‐Boryl Radicals via Concerted Electron‐Fluoride Transfer DOI
Xiao‐Song Xue,

Xueying Guo,

Yu‐Chen Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Abstract Selective C−F bond activation through a radical pathway in the presence of multiple C−H bonds remains formidable challenge, owing to extraordinarily strong strength bond. By aid density functional theory calculations, we disclose an innovative concerted electron‐fluoride transfer mechanism, harnessing unique reactivity Lewis base‐boryl radicals selectively activate resilient fluoroalkanes. This enables direct abstraction fluorine atom and subsequent generation alkyl radical, thus expanding boundaries halogen reactions.

Language: Английский

Recent advances of decatungstate photocatalyst in HAT process DOI
Praveen P. Singh, Surabhi Sinha, Prashant Gahtori

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2523 - 2538

Published: Jan. 1, 2024

The decatungstate anion (W

Language: Английский

Citations

28

Tetrabutylammonium decatungstate (TBADT), a compelling and trailblazing catalyst for visible-light-induced organic photocatalysis DOI
Bor‐Cherng Hong, Ranadheer Reddy Indurmuddam

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(19), P. 3799 - 3842

Published: Jan. 1, 2024

Tetrabutylammonium decatungstate (TBADT) has recently emerged as an intriguing photocatalyst under visible-light or near-visible-light irradiation in a wide range of organic reactions that were previously not conceivable. Given its ability to absorb visible light and excellent effectiveness activating unactivated chemical bonds, it is promising addition traditional photocatalysts. This review covers some the contemporary developments photocatalysis enabled by TBADT catalyst 2023, with contents organized reaction type.

Language: Английский

Citations

14

Radical hydroboration for the synthesis of organoboron compounds DOI
Yee Lin Phang, Ji‐Kang Jin, Feng‐Lian Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(32), P. 4275 - 4289

Published: Jan. 1, 2024

This review describes the recent research on radical hydroboration, which covers different boron sources including N-heterocyclic carbene borane, bis(pinacolato)diboron and pinacolborane, as well strategies in boryl generation.

Language: Английский

Citations

12

Light-promoted borylation and lactonization of propargyl acetates using NHC-borane DOI Creative Commons
Hangcheng Ni, Li Yu, Chaoming Li

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(6), P. 4652 - 4656

Published: Jan. 1, 2025

In the absence of photoredox catalyst, we achieved radical borylation and lactonization propargyl acetates under light irradiation using N-heterocyclic carbene borane, leading to synthesis substituted 4-(NHC-boryl)-2(5 H )-furanones.

Language: Английский

Citations

0

Stereodivergent Construction of Enamides via a Radical-Mediated Isodesmic Reaction DOI
Yingying Xu, Xin Zhang, X. Kang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6749 - 6759

Published: April 10, 2025

Language: Английский

Citations

0

Switchable Access to Mono‐ and Di‐Alkylated Boranes via Visible‐Light‐Induced Hydroboration of Alkenes with NHC‐Borane DOI Open Access

Xin Wu,

Yue Wang,

Ming‐Xi Zhou

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3824 - 3829

Published: Sept. 23, 2023

Abstract A photo‐induced metal‐free radical hydroboration of various styrenes with NHC‐borane has been developed, which can provide mono‐ and di‐alkylated boranes in a selective manner. Besides, this strategy also be applied to prepare di‐functionalized two different alkyl groups. Mild reaction conditions good functional groups compatibility were observed. Preliminary mechanism for was proposed.

Language: Английский

Citations

9

Visible-Light-Promoted Regioselective Hydroborylation of Ketene Dithioacetals with NHC-Boranes DOI
Yuanyuan An, Xiaolong Li,

Shuangshuang Xia

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15151 - 15158

Published: Oct. 18, 2023

NHC-boranes have been treated as a reliable source of boryl radicals. In this study, regioselective hydroborylation ketene dithioacetals with NHC-borane was achieved under mild conditions via visible-light-promoted radical chain process using thiophenol proton donor and hydrogen atom transfer. This protocol features low-cost catalyst, good functional group tolerance, relatively broad range substrate scope, to excellent yields. Moreover, mechanism reaction preliminarily studied.

Language: Английский

Citations

4

Metal-free C–H borylation of heterocycles by merging photoredox and hydrogen atom transfer catalysis DOI

Changfu Wu,

Shuang Luo,

Xiaozu Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4785 - 4793

Published: Jan. 1, 2024

Reported herein is a method that merges organophotoredox and hydrogen atom transfer catalysis to enable the C–H borylation of heterocycles using O 2 as an environmentally friendly oxidant.

Language: Английский

Citations

0

Quenching Rate Constants of Lewis Base‐Boryl Radical by Substrates: a Laser Flash Photolysis Study DOI
Fan Zhang, Yuanming Li, Xi Zhou

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Nov. 13, 2024

The advanced strategy using Lewis base-boryl radicals (LBRs) has recently been proposed for the addition of alkyl substituents to full-carbon quaternary center an organic molecule. However, as rate-determining step in whole route, reaction rate constants LBRs with substrates are extremely lacking. In this paper, 4-dimethylaminopyridine (DMAP)-BH2⋅ was selected a representative LBRs, and its reactions six monochloro-substituted substrates, including three methyl chlorobenzoates chlorinated acetanilides were studied experiments theoretical calculations. bimolecular constants, kq, determined laser flash photolysis approach. By comparing activation energies along two pathways, we have clarified attacking carbonyl oxygen instead chlorine atom. Furthermore, noncovalent interaction (NCI) analyses on these indicate that weak interactions, such hydrogen-bonding van der Waals significant influence reactivity substrates. Our study provides concrete clues extend synthetic strategy.

Language: Английский

Citations

0

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

Citations

0