Palladium-Catalyzed Desymmetric Coupling Reaction between Silacyclobutanes and Terminal Alkynes for the Synthesis of Silicon-Stereogenic Allyl Vinylsilanes DOI Creative Commons
Zhiyuan Chen, Zi‐Lu Wang, Jinbo Zhao

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 12, P. 100093 - 100093

Published: Sept. 7, 2024

Language: Английский

Catalytic asymmetric synthesis of silicon-stereogenic organosilanes DOI Creative Commons
Yichen Wu,

Long Zheng,

Yan Wang

et al.

Chem, Journal Year: 2023, Volume and Issue: 9(12), P. 3461 - 3514

Published: Oct. 19, 2023

Language: Английский

Citations

35

Regioselective Substitution of BINOL DOI Creative Commons
Lin Pu

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(10), P. 6643 - 6689

Published: May 9, 2024

1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at aromatic rings optically active BINOL developed one most convenient strategies to structurally modify for diverse applications. High regioselectivity achieved reaction with electrophiles. Depending upon conditions patterns, various functional groups can be introduced specific positions, such 6-, 5-, 4-, 3-positions, BINOL. Ortho-lithiation 3-position directed by 2-position have prepare 3- 3,3′-substituted BINOLs. use transition metal-catalyzed C–H activation also explored functionalize 3-, 7-positions. These regioselective substitutions allowed construction tremendous amount derivatives fascinating structures properties reviewed this article. Examples applications BINOLs varying catalysis, chiral sensing are provided.

Language: Английский

Citations

14

Enantioselective Copper‐Catalyzed Sequential Hydrosilylation of Arylmethylenecyclopropanes DOI
Bin Fu, Lianghua Wang, Kexin Chen

et al.

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

Published: July 18, 2024

Abstract Despite impressive advances in the construction of enantioenriched silacarbocycles featuring silicon‐stereogenic centers via a selection well‐defined sila‐synthons, development more convenient and economic method with readily available starting materials is significantly less explored remains considerable challenge. Herein, we report first example copper‐catalyzed sequential hydrosilylation accessible methylenecyclopropanes (MCPs) primary silanes, affording an efficient route to wide range chiral silacyclopentanes bearing consecutive silicon‐ carbon‐stereogenic excellent enantio‐ diastereoselectivities (generally ≥98 % ee, >25 : 1 dr). Mechanistic studies reveal that these reactions combine intermolecular ring‐opening aryl MCPs intramolecular asymmetric resultant Z / E mixture homoallylic silanes.

Language: Английский

Citations

8

Ligand-Controlled Regiodivergent Ring Expansion of Benzosilacyclobutenes with Alkynes en Route to Axially Chiral Silacyclohexenyl Arenes DOI

Xiaoxiao Tang,

Yulang Tang,

Ju Peng

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 21, 2024

A ligand-controlled regiodivergent and enantioselective ring expansion of benzosilacyclobutenes with internal naphthyl alkynes has been achieved by adjusting the ligand cavity size. The (

Language: Английский

Citations

7

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

16

Ruthenium-Catalyzed Sequential Hydrosilylation/Dehydrogenation and C–H Silylation: Synthesis of Six-Membered Indole Silacycles and Pyrrole Silyl Ether Cycles DOI

Jiefang Li,

Shanshan Xu,

Jieyu Liang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6142 - 6147

Published: July 12, 2024

Selective dehydrogenative C-H silylation is one of the most powerful tools to synthesize silacycles. Herein, we developed Ru-catalyzed sequential hydrosilylation/C-H allyl-indoles and O-H/C-H pyrrole phenols. Both six-membered indole silacycles silyl ether cycles were successfully synthesized with good functional group tolerance. Furthermore, RuHCl(CO)(PPh

Language: Английский

Citations

3

Modular and Regioselective Synthesis of Eight-Membered Benzosilacycles Enabled by Ring Expansion of Silacyclobutanes with Aryl Halides and Alkynes DOI
Zhenzhen Guo, Jinxiang Ye, Yingying Zhang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7066 - 7078

Published: April 16, 2025

Language: Английский

Citations

0

Rhodium/Ming-Phos-catalyzed asymmetric annulation reaction of silacyclobutanes with terminal alkynes DOI Creative Commons

Yue Sun,

Kaida Zhou,

Chun Ma

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 5(3), P. 205 - 210

Published: Sept. 7, 2023

Asymmetric ring-expansion reactions of silacyclobutanes (SCBs) with alkynes have evolved as one the powerful protocols for construction silicon-stereogenic compounds. However, achievement highly enantioselective annulation SCBs terminal remains a challenge. Herein, we report rhodium-catalyzed asymmetric reaction alkynes, which relies on newly identified chiral sulfinamide phosphine ligand Ming-Phos. This catalytic system exhibits unique effects under mild conditions, leading to direct synthesis structurally diverse silacycles in moderate good yields high enantioselectivities (up 95% ee).

Language: Английский

Citations

8

Recent Progress in the Synthesis of Silaspiranes DOI Open Access
Hua Chen, Xuejiao Hu,

Wanshu Wang

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(70)

Published: Sept. 23, 2023

Abstract Silaspiranes bearing a spiro‐silicon center are promising ring frameworks for the synthesis of novel spirocyclic molecules possessing unique properties. Development efficient methods towards these structures has therefore attracted considerable attentions synthetic chemists. This minireview highlights representative advances in field, and is categorized into four parts according to formation strategies: cyclization, annulation, expansion cycloaddition.

Language: Английский

Citations

7

Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds DOI Open Access

Yan Zeng,

Fei Ye

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(10), P. 3388 - 3388

Published: Jan. 1, 2023

In the past two decades, organosilicon compounds bearing silicon-stereogenic centers have attracted extensive attention in fields of organic synthesis, materials, and drug design.However, expansion these has been greatly restricted by limited source compounds.Therefore, development highly efficient selective asymmetric catalytic methods to obtain chiral with is a challenging task that needs be solved urgently.The latest research progress on new reaction systems for synthesis center containing organosilanes since 2011 mainly summarized.

Language: Английский

Citations

7