Cited by Transition-Metal-Catalyzed Cycloaddition of Small Ring Compounds

Chiral Silanols: Strategies and Tactics for Their Synthesis DOI

Jihui Gao,

Chuan He

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(19)

Published: Jan. 9, 2023

Silanols are valuable and important compounds, which have found widespread applications in the field of materials science, synthetic chemistry, medicinal chemistry. Although a handful approaches been developed for synthesis various silanols, access to enantioenriched silicon-stereogenic silanols remains underdeveloped. This Concept article intends summarize highlight recent advances construction endeavors encourage further research this area.

Language: Английский

Citations

Copper‐Catalyzed Asymmetric Synthesis of Silicon‐Stereogenic Benzoxasiloles DOI

Wan‐Er Gan,

Yong‐Shun Wu,

Bin Wu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(7)

Published: Jan. 5, 2024

Abstract A Cu‐catalyzed asymmetric synthesis of silicon‐stereogenic benzoxasiloles has been realized via intramolecular Si−O coupling [2‐(hydroxymethyl)phenyl]silanes. Cu(I)/difluorphos is found to be an efficient catalytic system for enantioselective Si−C bond cleavage and formation. In addition, kinetic resolution racemic substituted [2‐(hydroxymethyl)phenyl]silanes using Cu(I)/ PyrOx (pyridine‐oxazoline ligands) as the developed afford carbon‐ benzoxasiloles. Ring‐opening reactions chiral with organolithiums Grignard reagents yield various enantioenriched functionalized tetraorganosilanes.

Language: Английский

Citations

The role of silicon in drug discovery: a review DOI

Jenny‐Lee Panayides, Darren L. Riley, Felix Hasenmaile

et al.

RSC Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 15(10), P. 3286 - 3344

Published: Jan. 1, 2024

This review aims to highlight the role of silicon in drug discovery.

Language: Английский

Citations

Copper-catalyzed intermolecular Regio- and Enantioselective Hydrosilylation of Alkenes with Prochiral Silanes DOI

Xiaoyan Zhu,

Wenyu Gao,

Jian‐Lin Xu

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 3, 2025

This study presents a copper-catalyzed, substrate-controlled regio- and enantioselective intermolecular hydrosilylation method capable of accommodating broad scope alkenes prochiral silanes. The approach offers an efficient versatile pathway to generate enantioenriched linear branched alkyl-substituted Si-stereogenic Key features this reaction include mild conditions, simple catalytic systems, compatibility with diverse substrates, high yields enantioselectivities. While methods create chiral carbon centers stereochemically defined silicon have been developed, the ability both simultaneously would be value. Here authors present substratecontrolled

Language: Английский

Citations

Enantioselective Synthesis of 6/5-Spirosilafluorenes by Asymmetric Ring Expansion of 4/5-Spirosilafluorenes with Alkynes DOI

Hua Chen, Haixia Zhang,

Huimin Du

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(9), P. 1558 - 1563

Published: Feb. 27, 2023

A rhodium-catalyzed asymmetric ring expansion of 4/5-spirosilafluorenes with terminal alkynes has been developed using sterically demanding binaphthyl phosphoramidite ligand. The reaction is not only strategically distinct from cyclization or cycloaddition but also showcases the first enantioselective synthesis axially chiral 6/5-spirosilafluorenes.

Language: Английский

Citations

Synthetic strategies to access silacycles DOI

Fengjuan Chen, Luo Liu, Wei Zeng

et al.

Frontiers in Chemistry, Journal Year: 2023, Volume and Issue: 11

Published: June 15, 2023

In comparison with all-carbon parent compounds, the incorporation of Si-element into carboskeletons generally endows corresponding sila-analogues unique biological activity and physical-chemical properties. Silacycles have recently shown promising application potential in chemistry, pharmaceuticals industry, material chemistry. Therefore, development efficient methodology to assemble versatile silacycles has aroused increasing concerns past decades. this review, recent advances synthesis silacycle-system are briefly summarized, including transition metal-catalytic photocatalytic strategies by employing arylsilanes, alkylsilane, vinylsilane, hydrosilanes, alkynylsilanes, etc. as starting materials. Moreover, a clear presentation understanding mechanistic aspects features these developed reaction methodologies been high-lighted.

Language: Английский

Citations

Ring Expansion toward Disila‐carbocycles via Highly Selective C−Si/C−Si Bond Cross‐Exchange DOI

Min Liu,

Nuo Yan,

Haowen Tian

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(16)

Published: Feb. 23, 2024

Herein, we successfully inhibited the preferential homodimerization and C-Si/Si-H bond cross-exchange of benzosilacyclobutenes monohydro-silacyclobutanes achieved first highly selective C-Si/C-Si reaction by deliberately tuning Ni-catalytic system, which constitutes a powerful atom-economical ring expansion method for preparing medium-sized cyclic compounds bearing two silicon atoms at junction, are otherwise inaccessible. The DFT calculation explicitly elucidated pivotal role Si-H silacyclobutanes high strain substrates in realizing C-Si bonds cleavage reformation catalytic cycle.

Language: Английский

Citations

Enantioselective construction of Si-stereogenic linear alkenylhydrosilanes via copper-catalyzed hydrosilylation of alkynes DOI

Jian‐Lin Xu,

Zi‐Lu Wang, Jinbo Zhao

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(2), P. 100887 - 100887

Published: Jan. 15, 2024

Language: Английский

Citations

Photo-induced ring-maintaining hydrosilylation of unactivated alkenes with hydrosilacyclobutanes DOI

Shaowei Chen,

Meiyun Gao,

Xiaoqian He

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 12, 2025

Abstract Increasing attention has been paid to silacyclobutanes because of their wide application in ring opening and extension reactions. However, the synthesis functionalized remains an unmet challenge limited functional group tolerance reactions with organometallic reagents chlorosilacyclobutanes. Herein, we report a conceptually different solution this end through visible-light-induced metal-free hydrosilylation unactivated alkenes hydrosilacyclobutanes. A range diverse groups including base-sensitive acid, alcohol ketones participated reaction smoothly. In particular, first dihydrosilacyclobutane provides facile access various alkyl monohydrosilacyclobutanes. Unsymmetrical dialkyl have also synthesized consecutive one pot. The mechanism study reveals that Lewis basic solvent could promote generation strained silyl radicals by direct light irradiation without redox-active photocatalyst thiol catalyst plays important role accelerating reaction.

Language: Английский

Citations

Recent Advances in Transition Metal-Catalyzed C—Si Bond Cleavage of Silacyclobutanes DOI

Min Liu, Liping Qi, Dongbing Zhao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(10), P. 3508 - 3508

Published: Jan. 1, 2023

Due to the widespread application of various organosilicon compounds in material science, electronic devices and pharmaceutical research, it is great significance develop green efficient synthetic methods for diverse silicon-containing molecules.Silacyclobutane an important kind small-membered rings, which exhibits unique reactivities under transition metal catalysis cleave C-Si bond driven by inherent ring strain Lewis acidity.The resulting Si-M species can then be transformed into compounds.Herein, recent advances Pd, Rh, Ni-catalyzed cleavage reactions silacyclobutanes are summarized detail, mechanism development tendency such briefly discussed.

Language: Английский

Citations