In the presence of an allyl alcohol, α-chloroacetophenones undergo an allyloxycarbonylation reaction followed by in situ decarboxylative allylation to selectively afford the corresponding monoallylated ketones via a Pd-catalyzed domino sequence. The scope of the reaction was extended to substituted α-chloroacetophenones as well as various allyl alcohols.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c2cc32391e | DOI Listing |
J Org Chem
December 2024
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.
View Article and Find Full Text PDFJ Org Chem
December 2024
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China.
A novel Cu/Pd-catalyzed domino radical cyclization and C-H carbonylation of α-bromocarbonyls has been developed, which enables the rapid incorporation of CO unit into polycyclic quinolin-2(1)-one scaffolds. By using Mo(CO) as the CO source, the reaction proceeded smoothly to furnish various polycyclic carbonyl-containing quinolin-2(1)-one derivatives in high yields. Notably, this method could be used in the late-stage modification of biologically active molecules such as estrone.
View Article and Find Full Text PDFChem Commun (Camb)
July 2024
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
A method for the synthesis of furans bearing indoline skeletons was developed an intramolecular palladium-catalyzed 5- cyclization/etherification cascade of -propargyl arylamines containing a 1,3-dicarbonyl side chain. This method realized the first capture of vinyl carbopalladiums by ketones as -nucleophiles and showed a wide range of substrate tolerability affording trisubstituted furans in various yields. The enantioselective version for this domino process and diverse derivatizations of the reaction products were also studied.
View Article and Find Full Text PDFOrg Lett
May 2024
Key Laboratory of Synthetic and Natural Functional Molecule of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an, Shaanxi 710127, China.
J Am Chem Soc
April 2024
Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland.
Many elegant asymmetric syntheses of enantioenriched tertiary alcohols have been developed, and both the transition metal-catalyzed and the radical-based peripheral functionalization of tertiary alcohols have attracted intensive research interest in recent years. However, directly editing tetrasubstituted carbons remains challenging. Herein, we report a Pd-catalyzed migratory fluoroarylation reaction that converts tertiary alcohols to α-fluorinated tertiary alkyl ethers in good to excellent yields.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!