Synlett, Table of Contents Synlett 2018; 29(13): 1735-1740DOI: 10.1055/s-0036-1591602 letter © Georg Thieme Verlag Stuttgart · New York Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ–OH)Cl(IPr)}2] Sylwia Ostrowska a Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznań, Poland Email: pietrasz@amu.edu.pl , Szymon Rogalski a Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznań, Poland Email: pietrasz@amu.edu.pl , Jan Lorkowski a Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznań, Poland Email: pietrasz@amu.edu.pl , Jędrzej Walkowiak b Adam Mickiewicz University in Poznań, Centre for Advanced Technologies, Umultowska 89c, 61-614 Poznań, Poland , Cezary Pietraszuk * a Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznań, Poland Email: pietrasz@amu.edu.pl › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Dedicated to Professor Jacek Gawroński on the occasion of his 75th birthday. Abstract NHC–palladium(II) complex [{Pd(μ–OH)Cl(IPr)}2] (IPr = bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) catalyzes the oxidative coupling of a broad spectrum of aryl- and alkenylboronic acids at loadings down to 5 ppm. At the concentration of 0.05 mol% the catalyst permits an efficient reaction under base-free conditions. Keywords Keywordshomogeneous catalysis - palladium - NHC complexes - homocoupling - boronic acids Full Text References References and Notes 1 Aldemir H. Richarz R. Gulder TA. M. Angew. Chem. Int. Ed. 2014; 53: 8286 2 Bringmann G. Gunther C. Ochse M. Schupp O. Tasler S. In Progress in the Chemistry of Organic Natural Products . Vol. 82. Springer; Wien: 2001 3a Bringmann G. Price Mortimer AJ. Keller PA. Gresser MJ. Garner J. Breuning M. Angew. Chem. Int. Ed. 2005; 44: 5384 3b Wencel-Delord J. Panossian A. Leroux FR. Colobert F. Chem. Soc. Rev. 2015; 44: 3418 For reviews, see: 4a Cepanec I. Synthesis of Biaryls . Elsevier; Amsterdam: 2004 4b Hassan J. Sevignon M. 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The solution should be stored in the dark, no longer than 3 days). The mixture was stirred in air under reflux for 6 h. After completion of the reaction, the solvent was evaporated, the residue was dissolved in hexane (5 mL) and extracted with water (2 × 2 mL). The organic layer was dried over magnesium sulphate, and hexane was evaporated under reduced pressure. 159 mg of 4,4'-dimethylbiphenyl was obtained as a white solid. Yield = 94%. 1H NMR (300 MHz, CDCl3, ppm) δ: 7.50 (d, J = 8.1 Hz, 4H), 7.25 (d, J = 8.1 Hz, 4H), 2.41 (s, 6H); 13C NMR: (75 MHz, CDCl3, ppm) d: 138.3, 136.7, 129.4, 126.8, 21.1. MS (EI) m/z (%) = 182 (M+, 100), 167 (54), 152 (15). 22 Lee SJ. Gray KC. Paek JS. Burke MD. J. Am. Chem. Soc. 2008; 130: 466 23 Knapp DM. Gillis EP. Burke MD. J. Am. Chem. Soc. 2009; 131: 6961 24 Adamo C. Amatore C. Ciofini I. Jutand A. Lakmini H. J. Am. Chem. Soc. 2006; 128: 6829 25a Cai X. Majumdar S. George C. Fortman GC. Cazin CS. J. Slawin AM. Z. Lhermitte C. Prabhakar R. Germain ME. 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