A General and Efficient Catalyst for Palladium-Catalyzed C―O Coupling Reactions of Aryl Halides with Primary Alcohols

作者: Saravanan Gowrisankar , Alexey G. Sergeev , Pazhamalai Anbarasan , Anke Spannenberg , Helfried Neumann

DOI: 10.1021/JA103248D

关键词: Yield (chemistry)PalladiumOrganic chemistryRegioselectivityAlkylChemistryArylLigandCatalysisCoupling reaction

摘要: An efficient procedure for palladium-catalyzed coupling reactions of (hetero)aryl bromides and chlorides with primary aliphatic alcohols has been developed. Key to the success is synthesis exploitation novel bulky di-1-adamantyl-substituted bipyrazolylphosphine ligand L6. Reaction aryl halides including activated, nonactivated, as well gave corresponding alkyl ethers in high yield. Noteworthy, functionalizations presence secondary tertiary proceed excellent regioselectivity.

参考文章(74)
Rattan Gujadhur, D. Venkataraman, Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst Synthetic Communications. ,vol. 31, pp. 2865- 2879 ,(2001) , 10.1081/SCC-100105338
Jing Zhang, Mark Gandelman, Linda JW Shimon, Haim Rozenberg, David Milstein, None, Electron-Rich, Bulky Ruthenium PNP-Type Complexes. Acceptorless Catalytic Alcohol Dehydrogenation Organometallics. ,vol. 23, pp. 4026- 4033 ,(2004) , 10.1021/OM049716J
Rattan K. Gujadhur, Craig G. Bates, D. Venkataraman, Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts. Organic Letters. ,vol. 3, pp. 4315- 4317 ,(2001) , 10.1021/OL0170105
Franck Rataboul, Alexander Zapf, Ralf Jackstell, Surendra Harkal, Thomas Riermeier, Axel Monsees, Uwe Dingerdissen, Matthias Beller, New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides. Chemistry: A European Journal. ,vol. 10, pp. 2983- 2990 ,(2004) , 10.1002/CHEM.200306026
Grace Mann, Christopher Incarvito, Arnold L. Rheingold, John F. Hartwig, Palladium-Catalyzed C−O Coupling Involving Unactivated Aryl Halides. Sterically Induced Reductive Elimination To Form the C−O Bond in Diaryl Ethers Journal of the American Chemical Society. ,vol. 121, pp. 3224- 3225 ,(1999) , 10.1021/JA984321A
Jing Zhang, Gregory Leitus, Yehoshoa Ben-David, David Milstein, None, Facile Conversion of Alcohols into Esters and Dihydrogen Catalyzed by New Ruthenium Complexes Journal of the American Chemical Society. ,vol. 127, pp. 10840- 10841 ,(2005) , 10.1021/JA052862B
Andreas Ehrentraut, Alexander Zapf, Matthias Beller, Progress in the Palladium‐Catalyzed α‐Arylation of Ketones with Chloroarenes Advanced Synthesis & Catalysis. ,vol. 344, pp. 209- 217 ,(2002) , 10.1002/1615-4169(200202)344:2<209::AID-ADSC209>3.0.CO;2-5
Robin B. Bedford, Catherine S.J. Cazin, Debbie Holder, The development of palladium catalysts for CC and Cheteroatom bond forming reactions of aryl chloride substrates Coordination Chemistry Reviews. ,vol. 248, pp. 2283- 2321 ,(2004) , 10.1016/J.CCR.2004.06.012