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.

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