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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Palladium on Carbon-Catalyzed Cross-Coupling of Aryl Halides with Potassium p-Tolyltrifluoroborate in Air

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Pages 636-640 | Received 19 May 2008, Published online: 28 Jan 2009

REFERENCES

  • (a) Miyaura , N. ; Suzuki , A. Palladium-catalyzed cross-coupling reactions of organoboron compounds . Chem. Rev. 1995 , 95 , 2457 – 2483 ; (b) Suzuki , A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998 . J. Organomet. Chem. 1999 , 576 , 147 – 168 ; (c) Miyaura, N. In Topics in Current Chemistry; N. Miyaura (Ed.); Springer-Verlag: Berlin, 2002; vol. 219, p. 11; (d) Kotha, S.; Lahiri, K.; Kashinath, D. Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis. Tetrahedron 2002, 58, 9633–9695; (e) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419–2440; (f) Littke, A. F.; Fu, G. C. Palladium-catalyzed coupling reactions of aryl chlorides. Angew. Chem., Int. Ed. 2002, 41, 4176–4211 .
  • For comprehensive reviews see, (a) Felpi , F.-X. ; Ayad , T. ; Mitra , S. Pd/C: An old catalyst for new applications—Its use for the Suzuki–Miyaura reaction . Eur. J. Org. Chem. 2006 , 2679 – 2690 ; (b) Phan , N. T. ; Van Der Sluys , M. ; Jones , C. W. On the nature of the active species in palladium catalyzed Mizoroki–Heck and Suzuki–Miyaura couplings—Homogeneous or heterogeneous catalysis: A critical review . Adv. Synth. Catal. 2006 , 348 , 609 – 679 .
  • Although palladium leaching from the solid-supported catalysts can be an issue, we did not determine palladium levels in our isolated products: (a) Wallow , T. I. ; Novak , B. M. Highly efficient and accelerated Suzuki aryl couplings mediated by phosphine-free palladium sources . J. Org. Chem. 1994 , 59 , 5034 – 5037 ; (b) Davies , I. W. ; Matty , L. ; Hughes , D. L. ; Reider , P. J. Are heterogeneous catalysts precursors to homogeneous catalysts? J. Am. Chem. Soc. 2001 , 123 , 10139 – 10140 .
  • Molander , G. A. ; Ellis , N. Organotrifluoroborates: Protected boronic acids that expand the versatility of the Suzuki coupling reaction . Acc. Chem. Res. 2007 , 275 – 286 .
  • Molander , G. A. ; Biolatto , B. Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates . J. Org. Chem. 2003 , 68 , 4302 – 4314 .
  • Marck , G. ; Villiger , A. ; Buchecker , R. Aryl couplings with heterogeneous palladium catalysts . Tetrahedron Lett. 1994 , 35 , 3277 – 3280 .
  • Ishiyama , T. ; Kizaki , H. ; Hayashi , T. ; Suzuki , A. ; Miyaura , N. Palladium-catalyzed carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles: Synthesis of biaryl ketones . J. Org. Chem. 1998 , 63 , 4726 – 4731 .

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