New Three-Component Glyoxylation-Decarbonylative Stille Coupling Sequence to Acyl Heterocycles under Mild Conditions

Abstract

A consecutive sequence of glyoxylation of 1-methyl-1H-indole, 1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine or N-substituted pyrroles with oxalyl chloride and subsequent decarbonylative Stille coupling under very mild, Lewis acid free conditions using all reactants in equimolar quantities is reported. As an illustration, this glyoxylation-decarbonylative coupling sequence was elaborated into a consecutive, four-component synthesis of 1-methyl-3-(1-methyl-4,5-dihydro-1H-pyrazol-3-yl)-1H-indole.

Key words

glyoxylation - decarbonylative Stille reaction - multicomponent reaction - C-C coupling - acyl heterocycles

References

• 1 For a review on palladium-catalyzed carbonylative couplings, see: Brennführer A. Neumann H. Beller M. Angew. Chem. Int. Ed.  2009,  48:  4114 
• 2 Wynne JH. Lloyd CT. Jensen SD. Boson S. Stalick WM. Synthesis  2004,  2277 
• 3a Karpov AS. Merkul E. Rominger F. Müller TJJ. Angew. Chem. Int. Ed.  2005,  44:  6951 
• 3b Ahmed MSM. Mori A. Org. Lett.  2003,  5:  3057 
• 4 Stonehouse JP. Chekmarev DS. Ivanova NV. Lang S. Pairaudeau G. Smith N. Stocks MJ. Sviridov SI. Utkina LM. Synlett  2008,  100 
• 5 Nakao Y. Satoh J. Shirakawa E. Hiyama T. Angew. Chem. Int. Ed.  2006,  45:  2271 
• 6a Gooßen LJ. Paetzold J. Angew. Chem. Int. Ed.  2004,  43:  1095 
• 6b Gooßen LJ. Paetzold J. Angew. Chem. Int. Ed.  2002,  41:  1237 
• 7 Merkul E. Oeser T. Müller TJJ. Chem. Eur. J.  2009,  15:  5006 
• 8a Milstein D. Stille JK. J. Am. Chem. Soc.  1978,  100:  3636 
• 8b Milstein D. Stille JK. J. Org. Chem.  1979,  44:  1613 
• 8c Labadie JW. Stille JK. J. Am. Chem. Soc.  1983,  105:  6129 
• 9 Kashiwabara T. Tanaka M. J. Org. Chem.  2009,  74:  3958 
• 10a Liebeskind LS. Fengl RW. J. Org. Chem.  1990,  55:  5359 
• 10b Farina V. Kapadia S. Krishnan B. Wang C. Liebeskind LS. J. Org. Chem.  1994,  59:  5905 
• 10c Casado AL. Espinet P. Organometallics  2003,  22:  1305 
• 10d Han X. Stolz BM. Corey EJ. J. Am. Chem. Soc.  1999,  121:  7600 
• 10e Lu L. Burton DJ. Tetrahedron Lett.  1997,  38:  7673 
• 10f Ye J. Bhatt RK. Falck JR.
  J. Am. Chem. Soc.  1994,  116:  1 
• 10g Wang Y. Burton DJ. Org. Lett.  2006,  8:  1109 
• 11 Leibner JE. Jacobus J. J. Org. Chem.  1979,  44:  449 
• 12 Harrowven DC. Guy IL. Chem. Commun.  2004,  1968 
• 13 Renaud P. Lacote E. Quaranta L. Tetrahedron Lett.  1998,  39:  2123 
• 15a Adam MJ. Ruth TJ. Jivan S. Pate BD. J. Fluorine Chem.  1984,  25:  329 
• 15b Arnswald M. Neumann WP.
  J. Org. Chem.  1993,  58:  7022 

14

CCDC 775726 (compound 3b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; e-mail: [e-mail]].