Phosphonate-directed ortho C-H borylation of aromatic phosphonates is reported. Using simple starting materials and commercially accessible catalysts, this method provides steady access to -phosphonate arylboronic esters bearing pendant functionality and flexible substitution patterns. These products serve as flexible precursors for a variety of highly substituted phosphoarenes, and in situ downstream functionalization of the products is described.
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http://dx.doi.org/10.1021/jacs.0c04159 | DOI Listing |
Org Biomol Chem
January 2025
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, 473061, P. R. China.
A highly practical and efficient Cp*Co(III)-catalyzed C-H alkylation/alkenylation reaction of anilides with maleimides and acrylates was developed, during which a weakly coordinating amide carbonyl group functioned as the directing group. This approach features high efficiency, good functional group tolerance, and broad substrate scope, and a variety of 3-substituted succinimides and -alkenylated anilides were synthesized in moderate to excellent yields. Furthermore, the reaction is highly selective, affording mono--alkylated/alkenylated products only.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, Malaviya National Institute of Technology Jaipur, Jaipur 302017, Rajasthan, India.
J Am Chem Soc
January 2025
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Front Chem
December 2024
Department of Chemistry, University of Lucknow, Lucknow, India.
Rhodium(III) catalysis has been used for C-H activation of -nitrosoanilines with substituted allyl alcohols. This method provides an efficient synthesis of the functional -nitroso β-aryl aldehydes and ketones with low catalyst loading, high functional group tolerance, and superior reactivity of allyl alcohols toward -nitrosoanilines. We demonstrated that reaction also proceeds through the one-pot synthesis of -nitrosoaniline, followed by subsequent, C-H activation.
View Article and Find Full Text PDFChem Sci
January 2025
Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL) Pune 411 008 India
The isoquinoline core is present in one of the largest subsets of bioactive natural products. The multifunctional isoquinoline core exerts diverse bioactivity, resulting in the development of numerous isoquinoline-based drugs and molecules that are currently under clinical trials. We developed a new approach for phosphite-mediated [1,2] alkyl migration for an overall -C-H alkylation -alkylation of isoquinoline.
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