Aug 2026· Organic Letters· Vol 28 34, pp.
10659-10664
· 0 citations· 39 references
Medicine
Abstract
Aryl thianthrenium salt-mediated late-stage C-H carbonylation exhibits unique advantages in the site-selective modification of complex molecules. Herein, we disclose a palladium-catalyzed carbonylative esterification of aryl thianthrenium salts, in which commercially available potassium bromodifluoroacetate (BrCF2CO2K) is utilized as a safe and efficient CO surrogate. Carbon monoxide can be conveniently generated in situ via the reaction of the Pd(II)-difluorocarbene intermediate with water. This protocol features mild reaction conditions, low-cost and easily accessible raw materials, and high operational safety. It also possesses excellent functional group tolerance, thus serving as a practical strategy for the synthesis of high-value aromatic esters.
A palladium-catalyzed tandem Heck cyclization of N-(2-iodoaryl)acrylamides with N-methylanilines and ClCF2COONa has been developed for the synthesis of carbamoyl-substituted oxindoles bearing an all-carbon quaternary stereocenter, wherein difluorocarbene serves as the carbonyl source. This method operates under mild co...
Lu Wang, Yu-Lu Du, Yan-Rong Zhu et al.· Journal of Organic Chemistry· 0 citations
A regioselective palladium-catalyzed C3-H arylation of 1,2,4-triazolo[4,3-b]pyridazines with readily accessible aryl thianthrenium salts has been developed. This method provides direct access to a diverse array of C3-arylated triazolopyridazines in moderate to excellent yields under mild and operationally simple condit...
Na Wang, Pei-Feng Li, Li-Wen Xia et al.· Organic Letters· 0 citations
Herein, we report a one-step Pd(II)-catalyzed strategy for the synthesis of synthetically challenging and medicinally important functionalized dibenzotropone scaffolds from readily accessible o-alkynylaryl nitriles and electron-rich aryl boronic acids. The cascade process involves regioselective 1,2-syn-carbopalladatio...
Ayush Kumar, Sankar Sau, Amit Kumar· Organic Letters· 0 citations
Sulfoximines are indispensable core scaffolds in medicinal chemistry and organic synthesis. N-Allylation represents a powerful strategy for enriching the structural diversity of sulfoximines, while fluorine incorporation can effectively enhance the lipophilicity and metabolic stability of functional molecules. Herein,...
Ebrahim-Alkhalil M. A. Ahmed, Wen-Gen Cao, Shang-Hai Yu et al.· Journal of Organic Chemistry· 0 citations
An unprecedented Pd-catalyzed CO gas-free Narasaka-Heck carbonylation using Cr(CO)6 as a convenient carbonyl source has been developed for the step-economic construction of ester-containing pyrrolines. Notably, this method overcomes the limitations of conventional radical pathways, enabling compatibility with phenol-ty...
Xu-Meng Wang, Shan-Hua Yu, Jing Shang et al.· Journal of Organic Chemistry· 0 citations
Herein, we report a palladium-catalyzed, diazo-free, regioselective carbene coupling reaction of unactivated arenes with furyl carbenes, which are readily generated in situ from enynones, serving as safe and practical surrogates for traditional carbene sources. In this transformation, arenes are first thianthrenated, f...
