Palladium(II)-Catalyzed Oxidative ortho-Arylation of 2-Phenylpyridines

Abstract

A palladium(II)-catalyzed oxidative ortho-arylation of 2-phenylpyridines via direct C–H activation with aryl boric acids is described. The reaction could be conducted under mild conditions in the presence of Pd(OAc)₂/Cu(OTf)₂/TBHP system, and a variety of the azacyclic compounds bearing a biaryl unit were obtained with moderate to good yields.

Key words

palladium - C–H functionalization - ortho arylation - 2-phenylpyridines - arylboronic acid

• References

• 1a Roncali J. Chem. Rev. 1992; 92: 711
• 1b Pu L. Chem. Rev. 1998; 98: 2405
• 1c Kraft A, Grimsdale AC, Holmes AB. Angew. Chem. Int. Ed. 1998; 37: 402
• 1d Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
• 1e Bringmann G, Price Mortimer AJ, Keller PA, Gresser MJ, Garner J, Breuning M. Angew. Chem. Int. Ed. 2005; 44: 5384
• 1f MaGlacken GP, Bateman LM. Chem. Soc. Rev. 2009; 38: 2447

Selected reviews:
• 2a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
• 2b Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6723
• 2c Negishi E.-i. Angew. Chem. Int. Ed. 2011; 50: 6738
• 2d Farina V, Krishnamurphy V, Scott WJ. Org. React. 1998; 50: 1

Selected reviews:
• 3a Stuart DR, Fagnou K. Science 2007; 316: 1172
• 3b Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 3c Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
• 3d Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
• 3e Thansandote P, Lautens M. Chem. Eur. J. 2009; 15: 5874
• 3f Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
• 3g Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 3h Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
• 3i Ackermann L. Chem. Rev. 2011; 111: 1351
• 3j Mei T.-S, Kou L, Ma S, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778

Selected reviews:
• 4a Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
• 4b Pastine SJ, Gribkov DV, Sames D. J. Am. Chem. Soc. 2006; 128: 14220
• 4c Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
• 4d Shi Z, Li B, Wan X, Cheng J, Fang Z, Cao B, Qin C, Wang Y. Angew. Chem. Int. Ed. 2007; 46: 5554
• 4e Kakiuchi F, Kochi T. Synthesis 2008; 3013
• 4f Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
• 4g Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
• 4h Wasa M, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 9886
• 4i Wasa M, Worrell BT, Yu J.-Q. Angew. Chem. Int. Ed. 2010; 49: 1275
• 4j Xiao B, Fu Y, Xu J, Gong TJ, Dai JJ, Yi J, Liu L. J. Am. Chem. Soc. 2010; 132: 468
• 4k Gandeepan P, Parthasarathy K, Cheng C.-H. J. Am. Chem. Soc. 2010; 132: 8569
• 4l Ackermann L, Vicente R, Potukuchi HK, Pirovano V. Org. Lett. 2010; 12: 5032
• 4m Karthikeyan J, Cheng C.-H. Angew. Chem. Int. Ed. 2011; 50: 9880
• 5 Vogler T, Studer A. Org. Lett. 2008; 10: 130
• 6 Hong L, Wei W, Yuan X, Chao Z, Xiaobing W. Chem. Commun. 2011; 47: 1497
• 7a Chu J.-H, Tsai S.-L, Wu M.-J. Synthesis 2009; 3757
• 7b Sylvia K, Thomas V, Armido S. Synlett 2008; 2841
• 8 Aiso H, Kochi T, Mutsutani H, Tanabe T, Nishiyama S, Kakiuchi F. J. Org. Chem. 2012; 77: 7718
• 9 Engle KM, Thuy-Boun PS, Dang M, Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 18183