| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1313559 | Journal of Fluorine Chemistry | 2016 | 12 Pages |
•An efficient protocol for the palladium catalyzed Suzuki coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins has been achieved.•The dual role of TBAF·3H2O as a base and a solvating was found to be instrumental for the success of the reaction.•An assortment of 4-methyl-7-aryl coumarins were successfully synthesized using the optimized conditions.
A concise, efficient and facile protocol for the synthesis of a variety of 4-methyl-7-aryl/heteroaryl coumarins has been developed by utilizing the palladium catalyzed Suzuki cross-coupling reaction of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with a wide range of electronically diverse boronic acids under microwave irradiation. In the presence of a suitable catalyst, ligand and base, the coupling reaction proceeded smoothly to give the biaryls in satisfactory to exceptional yields. The dual role of TBAF·3H2O as a base as well as a solvating agent and the utilization of dppp as a ligand with moderate bite angle (91°) were found to be instrumental for the success of the reaction. Prominent features of this optimization conditions include: shorter reaction times, good to excellent yield and exceptional tolerance to a wide variety of functional groups.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideA concise, efficient and facile protocol for the synthesis of a variety of 4-methyl-7-aryl/heteroaryl coumarins has been developed by utilizing the palladium catalyzed Suzuki cross-coupling reaction of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with a wide range of electronically diverse boronic acids under microwave irradiation.
