Photocatalytic and Electrochemical Borylation and Silylation Reactions DOI Creative Commons

Tony Biremond,

Margaux Riomet, Philippe Jubault

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(11)

Published: June 26, 2023

Abstract Due to their high versatility borylated and silylated compounds are inevitable synthons for organic chemists. To escape the classical hydroboration/hydrosilylation paradigm, chemists turned attention more modern green methods such as photoredox chemistry electrosynthesis. This account focuses on novel generation of boryl silyl radicals forge C−B C−Si bonds from our group.

Language: Английский

Regioselective Hydro(deutero)silylation of 1,3-Enynes Enabled by Photoredox/Nickel Dual Catalysis DOI
Guodong Zhang, Wei Tan,

Duo Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 536 - 541

Published: Jan. 5, 2024

In the presence of visible light irradiation, organophoto/nickel dual catalysts, and mild base K2HPO4, 1,3-enynes react with silanecarboxylic acids to give corresponding α-silylallenes high selectivity. this uniquely decarboxylative hydrosilylation 1,3-enynes, a silyl radical process is involved diverse electron-rich -poor substrates proceed smoothly in moderate excellent yields. This transformation particularly synthetically worthwhile when using MeOD as solvent, which furnishes new access α-silyldeuteroallenes.

Language: Английский

Citations

13
Visible light catalyzed arylsilylation of alkenes to construct silicon-containing 1,1-diaryl moieties DOI
Jia Cao, Liuzhou Gao, Guoqiang Wang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4785 - 4791

Published: Jan. 1, 2024

We have developed an efficient photocatalyzed arylsilylation of alkenes, utilizing silylboranes and (hetero)aryl nitriles in the presence base photocatalyst.

Language: Английский

Citations

8
Visible-light-induced decarboxylative annulation of silanecarboxylic acids with 2‑isocyanobiaryls to 6‑silyl-substituted phenanthridines DOI

Cailin Deng,

Tiankai Zhang,

Ye Tian

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 560, P. 114098 - 114098

Published: April 12, 2024

Language: Английский

Citations

3
Photocatalyzed Deuterodichloromethylation of Olefins Using Silacarboxylic Acids as Halogen‐Atom Transfer Reagents DOI Open Access

Xin‐Long Yu,

Jiawei Hu, Jian Cao

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Abstract A visible‐light‐induced deuterodichloromethylation of alkenes was developed with readily available and inexpensive deuterochloroform as the reagent. Silacarboxylic acids, which could generate silyl radicals through efficient decarboxylation, were applied halogen atom transfer agents. series deuterium‐containing gem ‐dichloroalkanes prepared in good yields.

Language: Английский

Citations

0
Transition‐Metal‐Free Visible‐Light‐Induced Alkynylation of Silacarboxylic Acids DOI
Jun Dong, Yan-Fei Hu, Wendi Ma

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(15)

Published: April 1, 2025

Abstract An operationally simple and mild protocol for the visible‐light‐induced intermolecular coupling of silacarboxylic acids with sulfonyl alkynes to form alkynylsilanes is presented. This study highlights use inexpensive readily available 4CzIPN as a photocatalyst, along more stable silyl radical precursors, enabling synthesis variety in good excellent yields, notably without need transition metals. The transformation offers several key advantages, including broad substrate scope, functional group tolerance, compatibility heterocyclic substrates. Furthermore, both scale‐up reaction late‐stage functionalization natural products have been successfully achieved under conditions. These features make process not only efficient but also versatile suitable wide range applications chemical modification.

Language: Английский

Citations

0
Synthesis of Silylmethyl gem-Difluoroalkenes via Room-Temperature Catalytic Defluorosilylation of Trifluoromethylalkenes DOI

Seishu Ochiai,

Zhengyu Zhao,

Norio Shibata

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: June 5, 2025

We report the Cu-catalyzed defluorosilylation of trifluoromethylalkenes at room temperature, efficiently providing a diverse range silylmethyl-substituted gem-difluoroalkenes in excellent yields. Through careful optimization ligand and solvent conditions, reaction proceeded under notably mild enabling synthesis 37 distinct compounds, including several biologically relevant derivatives. This method significantly broadens synthetic access to silylmethyl-functionalized gem-difluoroalkenes, substantially enhancing their utility as valuable building blocks medicinal agrochemical chemistry.

Language: Английский

Citations

0
Metal-free photocatalyzed allylic silylation of allyl acetates and chlorides DOI

Xin-Long Yu,

Jia-Wei Hu,

Jian Cao

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4836 - 4842

Published: Jan. 1, 2023

A visible light-induced organophotocatalytic strategy for synthesizing functionalized allylsilanes through radical allylic silylation of allyl acetates and chlorides is reported.

Language: Английский

Citations

7
Decarboxylative Allylation of Silanecarboxylic Acids Enabled by Organophotocatalysis DOI
Guodong Zhang,

Kaiping Wang,

Duo Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7406 - 7411

Published: Oct. 2, 2023

Herein we present a visible-light-facilitated transition-metal-free allylic silylation reaction under mild conditions. This protocol is enabled by an inexpensive organophotocatalyst and provides efficient concise synthetic routes to substituted allylsilanes, particularly from readily available allyl sulfones stable silanecarboxylic acids as silyl radical precursors. Further investigations reveal that this strategy also generally compatible with vinyl access vinylsilanes. The silver catalytic system opens up alternative entry realize the decarboxylative allylation of acids.

Language: Английский

Citations

6
Photocatalyzed dehalogenative deuteration with silacarboxylic acids as halogen-atom transfer agents DOI
Jiawei Hu, Jian Cao, Li‐Wen Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4757 - 4761

Published: Jan. 1, 2024

A visible light-induced organophotocatalytic strategy for dehalogenative deuteration of a wide variety primary, secondary, and tertiary alkyl bromides is reported.

Language: Английский

Citations

2
Photocatalytic and Electrochemical Borylation and Silylation Reactions DOI Creative Commons

Tony Biremond,

Margaux Riomet, Philippe Jubault

et al.

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(11)

Published: June 26, 2023

Abstract Due to their high versatility borylated and silylated compounds are inevitable synthons for organic chemists. To escape the classical hydroboration/hydrosilylation paradigm, chemists turned attention more modern green methods such as photoredox chemistry electrosynthesis. This account focuses on novel generation of boryl silyl radicals forge C−B C−Si bonds from our group.

Language: Английский

Citations

3