Photoredox-catalyzed decarboxylative alkylation of silyl enol ethers has been developed. Diverse functionalized aryl alkyl ketones were afforded in modest to good yields using N-(acyloxy)phthalimide as an easy access alkyl radical source under mild and operationally simple conditions. The excellent performance of drug molecules such as fenbufen and indomethacin and naturally occurring carboxylic acids such as stearic acid and dehydrocholic acid further demonstrated the practicability of the reaction.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.7b03587DOI Listing

Publication Analysis

Top Keywords

photoredox-catalyzed decarboxylative
8
decarboxylative alkylation
8
alkylation silyl
8
silyl enol
8
enol ethers
8
functionalized aryl
8
aryl alkyl
8
alkyl ketones
8
ethers synthesize
4
synthesize functionalized
4

Similar Publications

Photoredox-Catalyzed Decarboxylation of Oxetane-2-Carboxylic Acids and Unique Mechanistic Insights.

Angew Chem Int Ed Engl

December 2024

Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan, 48109, United States.

Oxetanes are valuable motifs in medicinal chemistry applications, with demonstrated potential to serve as bioisosteres for an array of functional groups. Through the visible-light-mediated photoredox hydrodecarboxylation of 2-aryl oxetane 2-carboxylic acids this work enables access to the products of a [2+2]-photocycloaddition between alkenes and aryl aldehydes without the challenges associated with a traditional UV-light-mediated Paternò-Büchi reaction. Investigation into the hydrodecarboxylation mechanism reveals substrate-dependent modes of initiation under the conditions reported herein.

View Article and Find Full Text PDF

Visible-Light Photoredox-Catalyzed Direct Decarboxylative Functionalization of α-Keto Acids.

J Org Chem

October 2024

State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China.

A novel and environmentally friendly photocatalytic strategy is presented for generating acyl radicals from benzoylformic acids, which are subsequently trapped by various sulfone-based SOMOphiles. This strategy provides a robust toolkit to access a variety of synthetically important functionalized aryl-ketone derivatives, which efficiently and directly construct acyl-S, acyl-Se, acyl-C, and acyl-N bonds. The broad substrate scope, excellent functional group compatibility, and mild reaction conditions make this protocol practical and attractive.

View Article and Find Full Text PDF

Photoredox-catalyzed cross-coupling reaction is an efficient strategy for the construction of organic molecules. Herein, we developed a method to synthesize α-arylthioanisoles by constructing C-S bonds in the presence of a Ru-photoredox catalyst. Thus, a series of α-arylthioanisole compounds were efficiently obtained through decarboxylative cross-coupling under mild conditions.

View Article and Find Full Text PDF

Synthesis of -Alkyl Glycosides from Alkyl Bromides and Glycosyl Carboxylic Acids via Ni/Photoredox Dual Catalysis.

J Org Chem

August 2024

State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

-Alkyl glycosides, an important class of C-glycosides, are widely found in various drugs and natural products. The synthesis of -alkyl glycosides has attracted considerable attention. Herein, we developed a Ni/photoredox catalyzed decarboxylative ()-() coupling reaction of stable glycosylcarboxylic acids with simple aliphatic bromides to generate C-alkyl glycosides.

View Article and Find Full Text PDF

Photoredox-Catalyzed Sequential Decarboxylative/Defluorinative Aminoalkylation of CF-Alkenes with -Arylglycines.

Org Lett

July 2024

Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.

A photoredox-catalyzed sequential decarboxylative/defluorinative aminoalkylation of CF-alkenes with -arylglycines is described. This metal-free and redox-neutral protocol provided efficient access to the monofluoroalkenyl-1,5-diamines in good yields with excellent functional group compatibility. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the -difluoroalkenyl amine as an intermediate.

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!