An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developed via a B(CF)-catalyzed cycloaddition reaction of o-(1-alkynyl)(thio)anisoles or o-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.
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Sulfur and Oxygen Transfer Reactions with Simultaneous NHC-Coordination from Cyclic Thioureas and Ureas to a Stable Silylene.
Chemistry
December 2024
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, 980-8578, Japan.
Reactions of cyclic thioureas (1,3,4,5-tetramethylimidazol-2-thione and 1,3-dimethylimidazolidin-2-thione) and ureas (1,3,4,5-tetramethylimidazol-2-one and 1,3-dimethylimidazolidin-2-one) with an isolable dialkylsilylene were examined. In these reactions, cyclic thioureas served as sulfur and NHC (N-heterocyclic carbene) sources, and the corresponding silanethione and NHC-derived products formed via silanethione-NHC complexes. Reactions of cyclic ureas with the silylene afforded a new NHC and an isolable azomethine ylide.
View Article and Find Full Text PDFB(CF)-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds.
Chem Commun (Camb)
October 2020
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, China.
An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developed via a B(CF)-catalyzed cycloaddition reaction of o-(1-alkynyl)(thio)anisoles or o-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.
View Article and Find Full Text PDFSilicon and Oxygen's Bond of Affection: An Acyclic Three-Coordinate Silanone and Its Transformation to an Iminosiloxysilylene.
J Am Chem Soc
November 2017
WACKER-Chair of Macromolecular Chemistry, §WACKER-Institute of Silicon Chemistry, ⊥Catalysis Research Center, Technische Universität München, Lichtenbergstraße 4, 85748 Garching bei München, Germany.
A long-term dream comes true: An acyclic, neutrally charged silanone at last! Here, we report on the first examples of isolable acyclic, neutral, three-coordinate silanones 2 with indefinite stability as solids and lifetimes in solution of up to 2 days. The electronic properties of the Si═O bond were investigated via DFT calculations and revealed the π-donating N-heterocyclic imino (NHI) and σ-donating silyl groups as key factors for their enhanced stability. Besides initial reactivity studies of 2 toward CO and methanol, different isomerization pathways depending on the silyl substitution pattern were found.
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