1333433-54-7

Upstream product

• 14783-89-2 ortho-carboxybenzenediazonium tetrafluoroborate 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 55666-42-7 tert-butyl 2-bromobenzoate 
• 141-32-2 acrylic acid n-butyl ester 
• 1333433-52-5 C₁₈H₂₄O₄ 
• 1333433-53-6 (E)-2-(3-butoxy-3-oxoprop-1-en-1-yl)benzoic acid 

Downstream Products

• 1333433-43-4 (E)-butyl 3-(2-(methoxycarbamoyl)phenyl)acrylate 

Relevant academic research and scientific papers

Palladium(II)/Lewis Acid-Catalyzed Oxidative Olefination/Annulation of N-Methoxybenzamides: Identifying the Active Intermediates through NMR Characterizations

Although Pd(II)-catalyzed C-H activation in arenes has been widely successful in organic synthesis with many palladacycle compounds isolated as the intermediates in ligand-directed C-H activation, direct identification of the reaction intermediates such as the π-complex prior to the C-H activation is still not successful because of their instability. In the present study, we introduce a Pd(II)/LA (LA: Lewis acid)-catalyzed oxidative olefination/annulation reaction between N-methoxybenzamides and acrylates with oxygen as the oxidant source, in which two intermediates, including an unsymmetrical η6-complex and a palladacycle species without the proton releasing to the environment, were identified through NMR characterizations. The in situ formation of the heterobimetallic Pd(II)/LA species such as Pd(II)/Sc(III) may have enhanced the electrophilic properties of the Pd2+ cation, thus improving the stability of the π-complex, herein, an unsymmetrical η6-complex, and improving its catalytic efficiency. The observed insensitive electronic effect preferred the concerted metalation-deprotonation (CMD) mechanism for this C-H activation, and the detected palladacycle intermediate without the proton releasing to the environment offered an experimental clue to support the proposed CMD mechanism.

New heteroannulation reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H activation

A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Subs