A titanium(III)-catalysed intermolecular reductive coupling of ketones or imines with nitriles is described, which gives direct access to α-hydroxylated and α-aminated ketones. This coupling reaction is cross-selective and a catalytic version of the classical acyloin condensation. A reaction mechanism that is supported by first DFT calculations is discussed.
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http://dx.doi.org/10.1039/c3cc46894a | DOI Listing |
Nature
October 2024
Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.
The selective cross-coupling of two alkyl electrophiles to construct complex molecules remains a challenge in organic synthesis. Known reactions are optimized for specific electrophiles and are not amenable to interchangeably varying electrophilic substrates that are sourced from common alkyl building blocks, such as amines, carboxylic acids and halides. These limitations restrict the types of alkyl substrate that can be modified and, ultimately, the chemical space that can be explored.
View Article and Find Full Text PDFJ Am Chem Soc
July 2024
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Acceptorless dehydrogenative coupling reactions between C-H bonds offer straightforward and atom-economical methods connecting readily available materials while liberating gaseous hydrogen as the sole byproduct. Despite the growing interest in such transformations, their realization still poses a significant challenge. Here we report a photoinduced dehydrogenative coupling reaction of alkylamines with primary alcohols.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
June 2024
Department of Chemistry, University of California, Irvine, California, 92617, United States.
Nickel-catalyzed cross-electrophile coupling reactions of two aliphatic alcohol derivatives remain a challenge. Herein, we report a nickel-catalyzed reductive methylation reaction of aliphatic mesylates with methyl tosylate. This reaction provides straightforward access to compounds bearing aliphatic methyl groups from alkyl alcohol derivatives.
View Article and Find Full Text PDFJ Am Chem Soc
September 2023
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
Sensors (Basel)
May 2023
Faculty of Engineering, Ibb University, Ibb P.O. Box 70270, Yemen.
Detection and monitoring of airborne hazards using e-noses has been lifesaving and prevented accidents in real-world scenarios. E-noses generate unique signature patterns for various volatile organic compounds (VOCs) and, by leveraging artificial intelligence, detect the presence of various VOCs, gases, and smokes onsite. Widespread monitoring of airborne hazards across many remote locations is possible by creating a network of gas sensors using Internet connectivity, which consumes significant power.
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