Easy-to-execute carbonylations: microwave synthesis of acyl sulfonamides using Mo(CO)(6) as a solid carbon monoxide source.
The development of a robust palladium-catalyzed amidocarbonylation protocol for the preparation of aromatic acyl sulfonamides utilizing high-density microwave heating is described. This synthetic approach employs Mo(CO)(6) as a convenient CO-releasing reagent and allows for the direct preparation of acyl sulfonamides from both aryl iodides and aryl bromides. The reactions can be performed under air, employing only 15 min of microwave irradiation, to produce acyl sulfonamide derivatives in good to excellent yields. To illustrate the usefulness of this method, we reported the synthesis of a novel hepatitis C virus NS3 protease inhibitor.
Wu
Xiongyu
X
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, BMC, Box 574, SE-751 23 Uppsala, Sweden.
Rönn
Robert
R
Gossas
Thomas
T
Larhed
Mats
M
D002248:Carbon Monoxide; D020650:Combinatorial Chemistry Techniques; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D008872:Microwaves; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D013449:Sulfonamides / Q000138:chemical synthesis*; D013997:Time Factors; D017361:Viral Nonstructural Proteins / Q000037:antagonists & inhibitors*; D012697:Serine Endopeptidases; D043583:Nucleoside-Triphosphatase; D053487:DEAD-box RNA Helicases; D000085242:Viral Proteases
D002248:Carbon Monoxide; D004791:Enzyme Inhibitors; D008982:Molybdenum; D013449:Sulfonamides; D017361:Viral Nonstructural Proteins; C084422:NS3 protein, hepatitis C virus; D012697:Serine Endopeptidases; D043583:Nucleoside-Triphosphatase; D053487:DEAD-box RNA Helicases; D000085242:Viral Proteases