One-Step Conversion of Methyl Ketones to Acyl Chlorides.

J Org Chem

Lonza AG , Rottenstrasse 6, CH-3930 Visp, Switzerland.

Published: October 2015

Treatment of aromatic and heteroaromatic methyl ketones with sulfur monochloride and catalytic amounts of pyridine in refluxing chlorobenzene leads to the formation of acyl chlorides. Both electron-rich and electron-poor aryl methyl ketones can be used as starting materials. The resulting C1-byproduct depends on the precise reaction conditions chosen.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.5b01707DOI Listing

Publication Analysis

Top Keywords

methyl ketones
12
acyl chlorides
8
one-step conversion
4
conversion methyl
4
ketones acyl
4
chlorides treatment
4
treatment aromatic
4
aromatic heteroaromatic
4
heteroaromatic methyl
4
ketones sulfur
4

Similar Publications

TBAT-Catalyzed Dioxasilinane Formation from Beta-Hydroxy Ketones.

Tetrahedron

February 2025

Department of Chemistry, Western Washington University, Bellingham, WA 98225 (USA).

Beta-hydroxy ketones can be reduced using a sequence of ruthenium-catalyzed silyl etherification followed by tetrabutylammonium fluoride (TBAF) promoted intramolecular hydrosilylation. Switching from TBAF to tetrabutylammonium difluorotriphenylsilicate (TBAT), even without first forming the silyl ether, gave cyclic dioxasilinane products. These somewhat sensitive compounds could be isolated pure by column chromatography using florisil as the stationary phase.

View Article and Find Full Text PDF

In this study, raw milk was collected from three different grades of pastures and processed by pasteurization, blending and ultra-high temperature sterilization (UHT) in a factory production line with a feed size of 10 tons. Additionally, all samples (from raw milk to UHT milk samples) were analyzed by -nose and GC-MS. Key flavor compounds such as 2-heptanone, hexanal, nonanal, 3-methyl-butanal, and dimethyl sulfide were found.

View Article and Find Full Text PDF

Primary Roles of Branched Chain Amino Acids (BCAAs) and Their Metabolism in Physiology and Metabolic Disorders.

Molecules

December 2024

Department of Biochemistry and Molecular Biology, Graduate School of Medical Science, Yamagata University, Yamagata 990-9585, Japan.

Leucine, isoleucine, and valine are collectively known as branched chain amino acids (BCAAs) and are often discussed in the same physiological and pathological situations. The two consecutive initial reactions of BCAA catabolism are catalyzed by the common enzymes referred to as branched chain aminotransferase (BCAT) and branched chain α-keto acid dehydrogenase (BCKDH). BCAT transfers the amino group of BCAAs to 2-ketoglutarate, which results in corresponding branched chain 2-keto acids (BCKAs) and glutamate.

View Article and Find Full Text PDF

Even though α-arylation of ketones is attractive for direct C-H functionalization of organic substrates, the method largely relies on phosphine-ligated palladium complexes. Only recently, efforts have focused on developing nitrogen-based ligands as a more sustainable alternative to phosphines, with pyridine-functionalized pyridinium amidate (pyr-PYA) ,'-bidentate ligands displaying good selectivity and activity. Here, we report on a second generation set of catalyst precursors that feature a 5-membered N-heterocycle instead of a pyridine as chelating unit of the PYA ligand to provide less steric congestion for the rate-limiting transmetalation of the enolate.

View Article and Find Full Text PDF

C-H activation is the most direct way of functionalizing organic molecules. Many advances in this field still require specific directing groups to achieve the necessary activity and selectivity. Developing C-H activation reactions directed by native functional groups is essential for their broad application in synthesis.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!