The -difluoroallyl group is a sought-after structural motif commonly found in pharmaceutical compounds. Despite its appeal, achieving a controlled synthesis of both α,α- and γ,γ-difluoroallylated compounds has proven to be a challenging task. This study presents a new approach to difluoroallylation, which utilizes a regiodivergent C-H bond reaction catalyzed by ruthenium catalysis. This method enables the and C-H α,α- and C-H γ,γ-difluoroallylation of arenes using 3-bromo-3,3-difluoropropenes.
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http://dx.doi.org/10.1021/acs.orglett.3c00873 | DOI Listing |
J Org Chem
August 2024
Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53233, United States.
The catalytic system generated from the cationic Ru-H complex [(CH)(PCy)(CO)RuH]BF () with 2,3,4,5-tetrachloro-1,2-benzoquinone () was found to be highly effective for promoting the deaminative coupling reaction of 2-aminoaryl aldehydes with branched amines to form 2-substituted quinoline products. The analogous deaminative coupling reaction of 2-aminoaryl ketones with branched amines led to the regioselective formation of 2,4-disubstituted quinoline products. A number of biologically active quinoline derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using the catalytic method.
View Article and Find Full Text PDFNat Commun
July 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, 510641, Guangzhou, China.
Carboxylates are ideal directing groups because they are widely available, readily cleavable and excellent linchpins for diverse follow-up reactions. However, their use in meta-selective C-H functionalizations remains a substantial unmet catalytic challenge. Herein, we report the ruthenium-catalyzed meta-C-H alkylation of aromatic carboxylic acids with various functionalized alkyl halides.
View Article and Find Full Text PDFOrg Lett
June 2023
Shanghai Frontiers Science Center of Drug Target Identification and Delivery and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, College of Pharmaceutical Science, Shanghai Jiao Tong University, 800 Dongchuan Road, Minhang District, Shanghai 200240, China.
The -difluoroallyl group is a sought-after structural motif commonly found in pharmaceutical compounds. Despite its appeal, achieving a controlled synthesis of both α,α- and γ,γ-difluoroallylated compounds has proven to be a challenging task. This study presents a new approach to difluoroallylation, which utilizes a regiodivergent C-H bond reaction catalyzed by ruthenium catalysis.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!