4.7 Article

One-Pot Direct Synthesis of Siloles from 1-Bromo-2-silylethynylbenzenes or 1-Bromo-4-silyl-1,3-enynes

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Metal-Catalyzed Haloalkynylation Reactions

Mathis Kreuzahler et al.

Summary: Metal-catalyzed haloalkynylation reactions have revolutionized synthetic chemistry, especially with the recent rapid development in gold-catalyzed reactions. The choice of the catalytic system can significantly influence the regio- and stereoselectivity of the addition.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Inorganic & Nuclear

Synthesis of pyridine-fused siloles by ruthenium-catalyzed intramolecular hydrosilylation

Akinobu Naka et al.

Summary: The synthesis and ruthenium-catalyzed hydrosilylation reactions of 3-dimethylsilyl-2-ethynylpyridine derivatives (1a-1d) were described. Pyridine-fused siloles (2a and 2b) were obtained through intramolecular hydrosilylation of 1a and 1b in the presence of a ruthenium catalyst. The UV-Vis absorption and fluorescence properties of 2a and 2b were studied, and DFT calculations were performed to understand their photophysical properties.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Nickel(0)-Catalyzed Asymmetric Ring Expansion Toward Enantioenriched Silicon-Stereogenic Benzosiloles

Jinyu Zhang et al.

Summary: A novel strategy involving Ni-0-catalyzed ring expansion process was developed for the preparation of enantioenriched silicon-stereogenic benzosiloles, with promising applications in chiral electronic and optoelectronic devices. The catalysis strategy was also successfully applied to the asymmetric synthesis of silicon-stereogenic bis-silicon-bridged pi-extended systems, showing fluorescence emission, Cotton effects, and circularly polarized luminescence (CPL) activity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Nucleophilic Activation of Hydrosilanes via a Strain-Imposing Strategy Leading to Functional Sila-aromatics

Toshiya Ikeuchi et al.

Summary: Carefully designed cyclic hydrosilanes, combined with sterically demanding bidentate ligands of silicon, enable trans-selective hydrosilylation of unactivated alkynes, providing efficient access to diverse benzosiloles and related silacycles.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Asymmetric Synthesis of Silicon-Stereogenic Monohydrosilanes by Dehydrogenative C-H Silylation

Wei Yuan et al.

Summary: This method enables the synthesis of various asymmetrically trisubstituted 1H-benzosiloles and 1H-benzosilolome-tallocenes with good yields and excellent chemo-, regio-, and stereocontrol. The resulting silicon-stereogenic 1H-benzosilole compounds exhibit bright blue fluorescence and CPL signals, making them attractive to materials science practitioners.

ORGANIC LETTERS (2021)

Article Chemistry, Applied

Synthesis of Dibenzosiloles through Electrocatalytic Sila-Friedel-Crafts Reaction

Pan Han et al.

Summary: A novel electrocatalyzed method has been developed for the preparation of dibenzosiloles from biarylhydrosilanes using an intramolecular C-H/Si-H dehydrogenative coupling strategy. Both electro-donating and electro-withdrawing substitution groups were tolerated for this transformation, and the desired dibenzosilole products could be obtained in moderate to excellent yields. A sila-Friedel-Crafts reaction mechanism was proposed based on previous literature and controlled experiments.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Dithienylethene-Based Photochromic Siloles: A Straightforward and Divergent Synthetic Strategy

Marc Devillard et al.

Summary: A straightforward synthetic methodology for the preparation of photochromic siloles based on the dithienylethene motif has been developed. This method relies on an efficient palladium-catalyzed annulation reaction of a 2,3-bis(3-thienyl)-silirene with terminal alkynes in mild conditions. The reaction is functional group-tolerant and can be extended to the synthesis of photochromic polymers with different degrees of photochromic unit incorporation by adjusting the polymer/silirene stoichiometric ratio.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Facile and Convergent Synthesis of Highly Fused Oligosiloles by Rhodium-Catalyzed Stitching Reaction

Naoya Hamada et al.

Summary: A facile and convergent synthesis of highly fused oligosiloles was achieved by utilizing the rhodium-catalyzed stitching reaction, which allows up to 11 rings to be fused together in one synthetic operation. The synthesized compounds exhibit reversible electron acceptance under reducing conditions, suggesting potential applications in electronic devices.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Synthesis of Polysubstituted Germoles and Benzogermoles Using a Substoichiometric Amount of Diisobutylaluminum Hydride

Ko Kojima et al.

Summary: A synthetic route has been developed for the preparation of unsymmetrically polysubstituted germoles from 1-hydrogermyl-4-silyl-1,3-enynes with good to excellent yields. Adjustment of reaction conditions allows for the successful synthesis of other types of germines.

ORGANIC LETTERS (2021)

Article Materials Science, Multidisciplinary

Aggregation-induced emission from silole-based lumophores embedded in organic-inorganic hybrid hosts

Guanpeng Lyu et al.

Summary: Covalent grafting improves dispersibility of AIEgens, reduces scattering losses, increases photoluminescence quantum yields, and enhances chemical stability. Ureasil acts as a photoactive host that efficiently transfers excitation energy to embedded AIEgens.

JOURNAL OF MATERIALS CHEMISTRY C (2021)

Review Biochemistry & Molecular Biology

Advances in Synthesis of π-Extended Benzosilole Derivatives and Their Analogs

Tuan Thanh Dang et al.

MOLECULES (2020)

Article Chemistry, Multidisciplinary

The Combination of Cross-Hyperconjugation and σ-Conjugation in 2,5-Oligosilanyl Substituted Siloles

Alexander Poecheim et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Helicenes Built from Silacyclopentadienes via Ring-by-Ring Knitting of the Helical Framework

Oleg L. Tok et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Hybrid Metal/Organo Relay Catalysis Enables Enynes To Be Latent Dienes for Asymmetric Diels-Alder Reaction

Zhi-Yong Han et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Domino Cu-catalyzed C-N coupling/hydroamidation: A highly efficient synthesis of nitrogen heterocycles

Ruben Martin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)