A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3879047 | PMC |
| http://dx.doi.org/10.1021/ja409014v | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Rigid Stepladder Polymers Scandium-Catalyzed Polyspiroannulation of Quinoline with Alkyne.
J Am Chem Soc
January 2025
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Article Synopsis
- The study focuses on the development of a new type of rigid, three-dimensional polymers known as stepladder polymers, utilizing spirodihydroquinoline structures.
- These polymers are created through a reaction facilitated by a scandium catalyst that activates specific chemical bonds, allowing for the formation of complex structures from quinoline and alkyne compounds.
- The resulting polymers have increased thermal stability and porosity after undergoing a treatment that adds a methyl group to their nitrogen-containing functional groups.
Phosphite mediated molecular editing switch to -C-H alkylation of isoquinolines: emergence of a distinct photochemical [1,3] N to C rearrangement.
Chem Sci
December 2024
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.
View Article and Find Full Text PDFPalladium-Catalyzed Dual-Tasked -C-H Borylation of Aryl Iodides.
Org Lett
December 2024
School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, Shanghai 200092, People's Republic of China.
Article Synopsis
- A new method has been developed for Pd-catalyzed C-H borylation using maleimide to activate C-H bonds in aryl iodides.
- This reaction allows for the alkylation of -positions and borylation of -C-H bonds, leading to the synthesis of functionalized 3-aryl succinimides, which are important in various organic compounds.
- The boronate group created in this process can be further modified, showcasing the practical applications and potential of this C-H activation strategy for difunctionalizing aryl halides.
Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and -alkylamines.
Chem Commun (Camb)
December 2024
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061, China.
A palladium-catalyzed divergent reaction of primary benzamides using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, indanones are synthesized with moderate to good yields a Catellani reaction that involves sequential -C-H alkylation and -C-N bond cleavage annulation of primary benzamides. Employing norbornadiene (NBD) instead of NBE enables the assembly of -alkylamines by an intermolecular hydroamination reaction.
View Article and Find Full Text PDFRhodium-Catalyzed Meta-C-H Arylation of Arenes with Varied Linker Lengths: Bridging Catalytic Selectivity with Structural Diversity.
Angew Chem Int Ed Engl
November 2024
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400076, India.
The directing group (DG)-assisted approach has so far been the major route to achieve selective C-H activation at both proximal and distal positions. While rhodium catalysts are highly effective in DG-assisted ortho-C-H arylation, meta-C-H arylation with rhodium has not yet been reported. In this study, we present the first example of Rh-catalyzed meta-C-H arylation of arenes.
View Article and Find Full Text PDFWant 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!