Alkoxycarbonylation Reactions Performed Using Near-Stoichiometric Quantities of CO

Abstract

Alkoxycarbonylation reactions using near-stoichio­metric quantities of carbon monoxide gas are presented. The reactions are performed using microwave heating which, as well as the inherent advantages of rate acceleration, offers a convenient method for loading vessels with gases.

Key words

palladium - carbonylations - catalysis - water - microwave

References and Notes

• 1 For a recent overview, see: Catalytic Carbonylation Reactions, In Topics in Organometallic Chemistry   Vol. 18:  Beller M. Springer; Berlin: 2006. 
• 2 For an industrial perspective, see: Industrial Organic Chemistry Reactions   Weissermel K. Arpe H.-J. Wiley-VCH; Weinheim: 2003. 
• 3a Mori M. In Handbook of Organopalladium Chemistry for Organic Synthesis   Vol. 2:  Negishi E. Wiley-Interscience; New York: 2000.  p.2663 
• 3b Beller M. In Applied Homogeneous Catalysis with Organometallic Compounds   2nd ed., Vol. 1:  Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 2002.  p.145 
• 4 For general reviews of palladium-mediated carbonylation chemistry, see: Skoda-Földes R. Kollár L. Curr. Org. Chem.  2002,  6:  1097 
• For recent examples, see:
• 5a Neumann H. Brennführer A. Groß P. Riermeier T. Almena J. Beller M. Adv. Synth. Catal.  2006,  348:  1255 
• 5b Jimenez-Rodriguez C. Eastham GR. Cole-Hamilton DJ. Dalton Trans.  2005,  10:  1826 
• 5c Cai MZ. Zhao H. Huang YX. J. Mol. Catal. A: Chem.  2005,  238:  41 
• 6 For an example of the use of this chemistry on a multi-kg scale, see: Zapf A. Beller M. Top. Catal.  2002,  19:  101 
• 7 For a recent review, see: Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 
• 8 Kormos CM. Leadbeater NE. Synlett  2006,  1663 
• 9 Kormos CM. Leadbeater NE. Org. Biomol. Chem.  2007,  65 
• 10 Another solution to these problems can be the use of palladium catalysts bearing bidentate or monodentate phosphine ligands. The group of Beller and co-workers have been very successful in this approach. For an introduction to their work, see: Zapf A. Beller M. Chem. Commun.  2005,  431 
• 11 Vanier GS. Synlett  2007,  131 
• 12 Petricci E. Mann A. Schoenfelder A. Rota A. Taddei M. Org. Lett.  2006,  8:  3725 
• 13a Mägerlein W. Indolese AF. Beller M. J. Organomet. Chem.  2002,  641:  30 
• 13b Mägerlein W. Indolese AF. Beller M. Angew. Chem. Int. Ed.  2001,  40:  2856 
• 14 Gaviňo R. Pellegrini S. Castanet Y. Mortreux A. Mentré O. Appl. Catal. A: Gen.  2001,  217:  91 
• 15 Strategies using reagents that evolve CO upon heating have also been used. For a review, see: Morimoto T. Kakiuchi K. Angew. Chem. Int. Ed.  2004,  43:  5580