Aug 2026· Organic Letters· Vol 28 36, pp.
11231-11236
· 0 citations· 32 references
Medicine
Abstract
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 conditions. A broad substrate scope and excellent functional-group tolerance were observed for both coupling partners. The synthetic utility of the protocol was further demonstrated by gram-scale synthesis. Mechanistic studies, including competition and radical-trapping experiments, support a Pd(0)/Pd(II) catalytic pathway and rule out the involvement of radical intermediates. This work offers an efficient approach to the direct C3 functionalization of triazolopyridazines and highlights the potential of aryl thianthrenium salts as valuable arylation reagents in heterocycle synthesis.
A visible-light-induced sodium fluorescein-catalyzed four-component cascade reaction of N-arylpropiolamides, aryl thianthrenium salts, DABSO, and H2O has been developed, providing efficient access to diverse 3-sulfonyl-azaspiro[4.5]trienones in moderate to good yields. The reaction accommodates a broad range of aryl...
Zi-Tong Zhang, Yun Yang, Jian Li et al.· Journal of Organic Chemistry· 0 citations
A palladium-catalyzed (3 + 2) cycloaddition between arylalkynes and norbornene derivatives via C–H bond cleavage is reported. This reaction enables the selective synthesis of benzo-fused five-membered cyclic products from a variety of arylalkynes, including electronically biased and alkyl(aryl)alkynes. Notably, the u...
Sakura Takahashi, M. Tobisu, Y. Ano· ACS Catalysis· 0 citations
A Pd/Cu cocatalyzed synthesis of N-benzhydryl amines from aryl halides (electrophiles), N-tosylhydrazones (carbene equivalents), and anilines (nucleophiles) has been developed. The reaction operates under mild conditions and exhibits broad substrate scope and excellent functional group tolerance. The synthetic utility...
Yi-Fan Ping, Jian-Han Zhou, Dalton Raykowski et al.· Journal of the American Chem...· 1 citation
This study reports a simple and efficient photocatalytic radical cascade cyclization strategy for the one-step synthesis of allyl- and vinyl-sulfonyl fluorides bearing dibenzazepine or dioxodibenzothiazepine scaffolds. In contrast to the existing synthesis methods of allyl sulfonyl fluoride, this approach employs aryl-...
Jian-Hong Zhang, Yun-Qi Lin, Ye Fu et al.· Journal of Organic Chemistry· 0 citations
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)...
Shi-Biao Tang, Yang Yang, Su-Ping Zhang et al.· Organic Letters· 0 citations
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