Synthesis of Biaryl, Arylamine and Aryl Ketone Compounds Using a Commercially Available Air- and Moisture-Stable Palladium Catalyst

Abstract

A commercially available palladium complex bearing a N-heterocyclic carbene (NHC) was used in gram-scale synthesis of three compounds, a biaryl, an arylamine and an aryl ketone. The syntheses were performed in catalytic fashion using a Suzuki-Miyaura, a Buchwald-Hartwig and a ketone arylation reaction protocol. These three reactions were carried out using the same palladium pre-catalyst.

Key words

N-heterocyclic carbene - palladium - cross-coupling - ketone arylation - Suzuki-Miyaura coupling - aryl-amination

References

• 2a Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
• 2b Wolfe JP. Wagaw S. Marcoux JF. Buchwald SF. Acc. Chem. Res.  1998,  31:  805 
• 2c Hatrwig JF. Angew. Chem. Int. Ed.  1998,  37:  2046 
• For reviews, see:
• 3a Hermann W. Angew. Chem. Int. Ed.  2002,  41:  1290 
• 3b Hillier AC. Nolan SP. Platinum Metals Rev.  2002,  46:  50 
• 3c Hillier AC. Grasa GA. Viciu MS. Lee HM. Yang C. Nolan SP. J. Organomet. Chem.  2002,  653:  69 
• 3d Jafarpour L. Nolan SP. Adv. Organomet. Chem.  2000,  46:  181 
• 3e Weskamp T. Bohm VPW. Hermann WA. J. Organomet. Chem.  2000,  600:  12 
• 4a Huang J. Stevens ED. Nolan SP. Petersen JL. J. Am. Chem. Soc.  1999,  121:  2674 
• 4b Scholl M. Trnka TM. Morgan JP. Grubbs RH. Tetrahedron Lett.  1999,  40:  2247 
• 4c Ackermann L. Fürstner A. Weskamp T. Kohl FJ. Herrmann WA. Tetrahedron Lett.  1999,  40:  4748 
• 4d For saturated carbene complexes, see: Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett.  1999,  1:  1751 
• 5a Lee HM. Jiang T. Stevens ED. Nolan SP. Organometallics  2001,  20:  1255 
• 5b Hillier AC. Lee HM. Stevens ED. Nolan SP. Organometallics  2001,  20:  4246 
• 6 Grasa GA. Kissling RM. Nolan SP. Org. Lett.  2002,  4:  3583 
• 8a Hamann BC. Hartwig JF. J. Am. Chem. Soc.  1997,  119:  12382 
• 8b Palucki M. Buchwald SL. J. Am. Chem. Soc.  1997,  119:  11108 
• 8c Satoh T. Kawamura Y. Mirua M. Nomura M. Angew. Chem., Int. Ed. Engl.  1997,  36:  1740 
• 8d Terao Y. Fukuoka Y. Satoh T. Miura M. Nomura M. Tetrahedron Lett.  2002,  43:  101 
• 8e Fox JM. Huang X. Chieffi A. Buchwald SL. J. Am. Chem. Soc.  2000,  122:  1360 
• 9a Wolfe JP. Wagaw S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res.  1998,  31:  805 
• 9b Hartwig JF. Acc. Chem. Res.  1998,  31:  852 
• 10a For a review, see: Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
• 10b Suzuki A. Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998.  p.49-97  ; and references cited therein
• 10c Hamann BC. Hartwig JF. J. Am. Chem. Soc.  1998,  120:  7369 
• 10d Reetz MT. Lohmer G. Schwickardi R. Angew. Chem., Int. Ed. Engl.  1998,  37:  481 
• 10e Littke AF. Fu GC. J. Org. Chem.  1999,  64:  10 
• 11 Arduengo AJ. Acc. Chem. Res.  1999,  32:  913 
• 12a Collman JP. Hegedus LS. Norton JR. Finke RG. Principles and Applications of Organotransition Metal Chemistry   University Science; Mill Valley, CA: 1987. 
• 12b Parshall GW. Ittel S. Homogeneous Catalysis   Wiley; New York: 1992. 
• 12c Homogeneous Catalysis with Metal Phosphine Complexes   Pignolet LH. Plenum; New York: 1983. 
• 13 Viciu MS. Kissling RM. Stevens ED. Nolan SP. Org. Lett.  2002,  4:  2229 
• 14 Jafarpour L. Nolan SP. J. Organomet. Chem.  2001,  617:  17 
• 15a Viciu MS. Germaneau RF. Navarro O. Stevens ED. Nolan SP. Organometallics  2002,  21:  5470 
• 15b Viciu MS. Germaneau RF. Nolan SP. Org. Lett.  2002,  4:  4053 
• 16 Kawatsura M. Hartwig JF. J. Am. Chem. Soc.  1999,  121:  1473 
• 17 Barluenga J. Aznar F. Fernandez M. Chem.-Eur. J.  1997,  3:  1629 
• 18 Wolfe JP. Singer RA. Yang BY. Buchwald SL. J. Am. Chem. Soc.  1999,  121:  9550 

1

Visiting student from the Université Pierre et Marie Curie.

7

Complex 1 is now commercially available from Strem Chemicals Inc.