The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp(2) and sp(3) C-H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in tert-amyl alcohol or water solvent at 100-140 °C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. The picolinic acid auxiliary is used for amine γ-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid β-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3829615 | PMC |
| http://dx.doi.org/10.1021/jo4013628 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Facile Access to Quaternary Carbon Centers via Ni-Catalyzed Arylation of Alkenes with Organoborons.
J Am Chem Soc
January 2025
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.
Quaternary carbon centers are widespread structural motifs, thus representing extensive interest in organic synthesis. We describe here an efficient nickel-catalyzed intermolecular, -selective arylation of minimally functionalized alkenes with stable organoborons, affording a broad range of cyclic or acyclic quaternary carbon centers under mild conditions. The utilization of the diimine ligand is critical for high reactivity and chemoselectivity.
View Article and Find Full Text PDFRegio- and Enantioselective Rhodium-Catalyzed Allylic Arylation of Racemic Allylic Carbonates with Arylboronic Acids.
Angew Chem Int Ed Engl
January 2025
New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Rhodium-catalyzed regio- and enantioselective allylic arylation of racemic alkyl- and aryl- substituted allylic carbonates with arylboronic acids using commercially available BIBOP ligand is reported. This reaction proceeds at room temperature without base or other additive to deliver allylic arylation products in excellent yields, regio- and enantioselectivity (up to 95 % yield, >20 : 1 b/l, >99 % ee). Rh/BIBOP is disclosed as an efficient catalytic system for allylic substitution reaction.
View Article and Find Full Text PDFBenzothiazolium salts as versatile primary alcohol derivatives in Ni-catalyzed cross-electrophile arylation/vinylation.
Org Biomol Chem
January 2025
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.
Herein, we report a Ni-catalyzed cross-electrophile coupling of aryl/vinyl halides with benzothiazolium salts derived from alcohols. Our findings demonstrate that primary alkyl benzothiazolium salts serve as effective C(sp)-O substrates, facilitating coupling with aryl and vinyl halides. This method not only enables the formal functionalization of primary alcohols but also provides experimental support for previously established sequential alcohol halogenation and Ni-catalyzed reductive coupling platforms.
View Article and Find Full Text PDFNew Insights into the Modifications and Bioactivities of Indole-3-Carboxaldehyde and its Derivatives as a Potential Scaffold for Drug Design: A Mini-Review.
Mini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFAnisole Processible n-Type Conjugated Polymers Synthesized via C─H/C─H Oxidative Direct Arylation Polycondensation for Organic Electrochemical Transistors.
Macromol Rapid Commun
November 2024
School of Materials Science and Engineering, Tianjin Key Laboratory of Molecular Optoelectronic Science and Key Laboratory of Organic Integrated Circuits, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Ministry of Education, Tianjin University, Tianjin, 300072, P. R. China.
Article Synopsis
- The study focuses on addressing the shortage of n-type polymers for organic electrochemical transistors (OECTs), which are crucial for electronic devices.
- It introduces three new polymers synthesized using an environmentally friendly method called oxidative direct arylation polycondensation (Oxi-DArP), which utilizes unfunctionalized monomers.
- Among them, the polymer gTzDPP-C8 demonstrated exceptional performance, achieving high transconductance and capacitance, highlighting the effectiveness of this new synthesis method for creating high-performance n-type organic materials.
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!