Microwave-Promoted Hydroxycarbonylation in Water Using Gaseous Carbon Monoxide and Pre-Pressurized Reaction Vessels

Abstract

The microwave-promoted hydroxycarbonylation of aryl iodides using reaction vessels pre-pressurized with CO is reported. Reactions are performed using simple palladium salts with loadings of either 0.01 mol% or 1 mol%.

Key words

palladium - carbonylations - catalysis - water - microwave

References and Notes

• A number of books on microwave-promoted synthesis have been published recently:
• 1a Kappe CO. Stadler A. Microwaves in Organic and Medicinal Chemistry   Wiley-VCH; Weinheim: 2005. 
• 1b Microwave-Assisted Organic Synthesis   Lidström P. Tierney JP. Blackwell; Oxford: 2005. 
• 1c Microwaves in Organic Synthesis   Loupy A. Wiley-VCH; Weinheim: 2002. 
• 1d Hayes BL. Microwave Synthesis: Chemistry at the Speed of Light   CEM Publishing; Matthews NC: 2002. 
• 2 For a recent review, see: Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 
• For other reviews on the general area of microwave-promoted organic synthesis, see:
• 3a Larhed M. Moberg C. Hallberg A. Acc. Chem. Res.  2002,  35:  717 
• 3b Lew A. Krutzik PO. Hart ME. Chamberlain AR. J. Comb. Chem.  2002,  4:  95 
• 3c Lidström P. Tierney JP. Wathey B. Westman J. Tetrahedron  2001,  57:  9225 
• 4 Gronnow MJ. White RJ. Clark JH. Macquarrie DJ. Org. Process Res. Dev.  2005,  9:  516 
• 5 Milijanic O. Vollhardt KPC. Whitener GD. Synlett  2003,  29 
• 7 Kaval N. Dehaen W. Kappe CO. Van der Eycken E. Org. Biomol. Chem.  2004,  2:  154 
• 9 For an overview of the apparatus, see: Stadler A. Yousefi BH. Dallinger D. Walla P. Van der Eycken E. Kaval N. Kappe CO. Org. Process Res. Dev.  2003,  7:  707 
• 10 For a review of palladium-mediated carbonylation chemistry, see: Skoda-Földes R. Kollár L. Curr. Org. Chem.  2002,  6:  1097 
• For examples, see:
• 11a Magerlein W. Indolese AF. Beller M. Angew. Chem. Int Ed.  2001,  40:  2856 
• 11b Albaneze-Walker J. Bazaral C. Leavey T. Dormer PG. Murry JA. Org. Lett.  2004,  6:  2097 
• 11c Calo V. Giannoccaro P. Nacci A. Monopoli A. J. Organomet. Chem.  2002,  645:  152 
• 11d Ramesh C. Nakamura R. Kubota Y. Miwa M. Sugi Y. Synthesis  2004,  501 
• 12 For a general review of alternatives to CO gas, see: Morimoto T. Kakiuchi K. Angew. Chem. Int. Ed.  2004,  43:  5580 
• For examples, see:
• 13a Lagerlund O. Larhed M. J. Comb. Chem.  2006,  8:  4 
• 13b Wu X. Larhed M. Org. Lett.  2005,  7:  3327 
• 13c Wu XY. Nilsson P. Larhed MJ. J. Org. Chem.  2005,  70:  346 
• 13d Wannberg J. Larhed M. J. Org. Chem.  2003,  68:  5750 
• 14 For a review see: Leadbeater NE. Chem. Commun.  2005,  2881 
• 15 Beletskaya IP. Lapidus AL. Petrovskii KB. Russ. J. Org. Khim.  1998,  34:  1528 
• 16 Monteil F. Kalck P. J. Organomet. Chem.  1994,  482:  45 
• 17 Uozumi Y. Watanabe T. J. Org. Chem.  1999,  64:  6921 
• 18 Mizushima E. Hayashi T. Tanaka M. Top. Catal.  2004,  29:  163 
• 19 Arvela RK. Leadbeater NE. Sangi MS. Williams VA. Granados P. Singer RS. J. Org. Chem.  2005,  70:  161 
• 20a Arvela RK. Leadbeater NE. Mack TM. Kormos CM. Tetrahedron Lett.  2006,  47:  217 
• 20b Arvela RK. Leadbeater NE. Org. Lett.  2005,  7:  2101 
• 21 Leadbeater NE. Marco M. J. Org. Chem.  2003,  68:  5660 
• 22 Herrmann WA. Reisinger CP. Ofele K. Brossmer C. Beller M. Fischer H. J. Mol. Catal. A: Chem.  1996,  108:  51 

6

Specially designed reactors have been used for gas phase catalysis under microwave irradiation. See ref. 7 and references therein.

8

Synthos 3000 available from Anton Paar GmbH (www.anton-paar.com).