Hydroxymethyldiphenylsilane

• CAS: 778-25-6
• Catalog Number: ACM778256
• Category: Main Products
• Molecular Weight: 214.34
• Molecular Formula: C13H14OSi

Case Study

Methyldiphenylsilanol as a Key Transmetallating Agent in Palladium-Catalyzed Carbonylative Cross-Coupling

Li, Xiong, et al. Advanced Synthesis & Catalysis 362.19 (2020): 4078-4083.

A palladium-catalyzed, external-CO-free carbonylative Hiyama-Denmark cross-coupling has been developed. Using silylcarboxylic acids as bifunctional reagents that release CO and supply the silicon nucleophile eliminates the need for gaseous CO and a pre-formed silylarene. The protocol tolerates a wide range of functional groups and is effective with electron-rich, -neutral, and -deficient aryl iodides. Stoichiometric and control experiments were performed to probe the mechanism and corroborate the proposed dual role of the silylcarboxylic acids.
Mechanistic insight was obtained from several key experiments. Heating a THF solution of 1-iodo-4-methoxybenzene (1a) with stoichiometric Pd(dba)2 and ligand L6 at 50 °C for 5 h afforded the oxidative-addition complex I in 19% yield, and its identity was confirmed by X-ray crystallography. Under CO (THF, 50 °C) complex I cleanly converted to the CO-insertion (acyl) complex II, which was isolated in 90% yield. Replacing PdI2 with preformed complex I under the standard catalytic conditions delivered product 3a in 80% yield. Treating isolated complex II with methyldiphenylsilanol in NMP in the presence of 2.0 equiv of Cu-2 and 2.7 equiv of CsF gave 3a in 50% yield, demonstrating that the silanol (after activation) can act as a transmetallating agent.

Custom Q&A

What is the molecular formula of Hydroxymethyldiphenylsilane?

The molecular formula of Hydroxymethyldiphenylsilane is C13H14OSi.

What are some synonyms for Hydroxymethyldiphenylsilane?

Some synonyms for Hydroxymethyldiphenylsilane are Methyldiphenylsilanol, Silanol, methyldiphenyl-, and Diphenylmethylsilanol.

What is the molecular weight of Hydroxymethyldiphenylsilane?

The molecular weight of Hydroxymethyldiphenylsilane is 214.33 g/mol.

When was Hydroxymethyldiphenylsilane created?

Hydroxymethyldiphenylsilane was created on March 27, 2005.

What is the IUPAC name of Hydroxymethyldiphenylsilane?

The IUPAC name of Hydroxymethyldiphenylsilane is hydroxy-methyl-diphenylsilane.

What is the InChI of Hydroxymethyldiphenylsilane?

The InChI of Hydroxymethyldiphenylsilane is InChI=1S/C13H14OSi/c1-15(14,12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11,14H,1H3.

What is the InChIKey of Hydroxymethyldiphenylsilane?

The InChIKey of Hydroxymethyldiphenylsilane is MLPRTGXXQKWLDM-UHFFFAOYSA-N.

What is the canonical SMILES of Hydroxymethyldiphenylsilane?

The canonical SMILES of Hydroxymethyldiphenylsilane is C[Si](C1=CC=CC=C1)(C2=CC=CC=C2)O.

What is the CAS number of Hydroxymethyldiphenylsilane?

The CAS number of Hydroxymethyldiphenylsilane is 778-25-6.

What is the European Community (EC) number of Hydroxymethyldiphenylsilane?

The European Community (EC) number of Hydroxymethyldiphenylsilane is 212-293-4.