Title:
PALLADIUM-CATALYSED CARBON-CARBON BOND FORMING REACTIONS IN COMPRESSED CARBON DIOXIDE
Document Type and Number:
WIPO Patent Application WO2003009936
Kind Code:
A3
Abstract:
A palladium-catalysed carbon-carbon bond forming reaction in compressed carbon dioxide is provided wherein at least one of the reagents used in said reaction is bounded to a solid polymer support. In a second aspect, a palladium-catalysed carbon-carbon bond forming reaction in compressed carbon dioxide is provided wherein said reaction is performed in the presence of a tetra-alkylammonium acetate. In a third aspect, a palladium-catalysed carbon-carbon bond forming reaction in compressed carbon dioxide is provided wherein said palladium catalyst does not have any fluorinated phosphine ligands but does have at least one phosphine ligand that has at least one substituent that is selected from tert-alkyl groups, cycloalkyl groups and optionally substituted phenyl groups or 1'-diphenylphosphino-biphenyl. In a fourth aspect, there is provided a palladium-catalysed Suzuki or Heck reaction in compressed carbon dioxide wherein both of the substrates being combined in said reactions are boronic acids.
Inventors:
HOLMES ANDREW BRUCE (GB)
GORDON RICHARD S (GB)
EARLY TESSA R (GB)
GORDON RICHARD S (GB)
EARLY TESSA R (GB)
Application Number:
PCT/GB2002/003361
Publication Date:
August 21, 2003
Filing Date:
July 23, 2002
Export Citation:
Assignee:
HOLMES ANDREW BRUCE (GB)
GORDON RICHARD S (GB)
EARLY TESSA R (GB)
GORDON RICHARD S (GB)
EARLY TESSA R (GB)
International Classes:
B01J3/00; B01J31/04; B01J31/06; B01J31/16; B01J31/18; B01J31/24; C07B37/04; C07C1/32; C07C41/30; C07C51/09; C07C67/343; C07C205/06; C07C205/56; B01J23/44; (IPC1-7): B01J23/44; B01J31/16; B01J31/24; C07B37/04; C07F5/02
Domestic Patent References:
| WO1999038820A1 | 1999-08-05 | |||
| WO2001014289A2 | 2001-03-01 |
Other References:
GORDON RICHARD S. ET AL: "Palladium-mediated cross-coupling reactions with supported reagents in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, 25 February 2002 (2002-02-25), pages 640 - 641, XP002232828, ISSN: 1359-7345
EARLY TESSA R ET AL: "Palladium-catalysed cross-coupling reactions in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, 19 September 2001 (2001-09-19), pages 1966 - 1967, XP002232829, ISSN: 1359-7345
OSSWALD T ET AL: "Stille couplings in supercritical CO2 catalyzed with perfluoro-tagged and un-tagged Pd complexes", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 42, no. 16, 16 April 2001 (2001-04-16), pages 2965 - 2967, XP004232364, ISSN: 0040-4039
JEFFERY T: "On the Efficiency of Tetraalkylammonium Salts in Heck Type Reactions", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 52, no. 30, 22 July 1996 (1996-07-22), pages 10113 - 10130, XP004104052, ISSN: 0040-4020
MORITA D K: "Palladium-catalyzed cross-coupling reactions in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, no. 13, 1998, pages 1397 - 1398, XP002102061, ISSN: 1359-7345
BELETSKAYA IRINA P ET AL: "The Heck Reaction as a Sharpening Stone of Palladium Catalysis", CHEMICAL REVIEWS, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 100, no. 8, 2000, pages 3009 - 3066, XP002199991, ISSN: 0009-2665
SHEZAD NAJAM ET AL: "Use of Fluorinated Palladium Sources for Efficient Pd-catalysed Coupling Reactions in Supercritical Carbon Dioxide", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 40, 1999, pages 2221 - 2224, XP002232830, ISSN: 0040-4020
CARROLL M A: "Palladium-catalysed carbon-carbon bond formation in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, no. 13, 1998, pages 1395 - 1396, XP002102060, ISSN: 1359-7345
EARLY TESSA R ET AL: "Palladium-catalysed cross-coupling reactions in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, 19 September 2001 (2001-09-19), pages 1966 - 1967, XP002232829, ISSN: 1359-7345
OSSWALD T ET AL: "Stille couplings in supercritical CO2 catalyzed with perfluoro-tagged and un-tagged Pd complexes", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 42, no. 16, 16 April 2001 (2001-04-16), pages 2965 - 2967, XP004232364, ISSN: 0040-4039
JEFFERY T: "On the Efficiency of Tetraalkylammonium Salts in Heck Type Reactions", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 52, no. 30, 22 July 1996 (1996-07-22), pages 10113 - 10130, XP004104052, ISSN: 0040-4020
MORITA D K: "Palladium-catalyzed cross-coupling reactions in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, no. 13, 1998, pages 1397 - 1398, XP002102061, ISSN: 1359-7345
BELETSKAYA IRINA P ET AL: "The Heck Reaction as a Sharpening Stone of Palladium Catalysis", CHEMICAL REVIEWS, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 100, no. 8, 2000, pages 3009 - 3066, XP002199991, ISSN: 0009-2665
SHEZAD NAJAM ET AL: "Use of Fluorinated Palladium Sources for Efficient Pd-catalysed Coupling Reactions in Supercritical Carbon Dioxide", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 40, 1999, pages 2221 - 2224, XP002232830, ISSN: 0040-4020
CARROLL M A: "Palladium-catalysed carbon-carbon bond formation in supercritical carbon dioxide", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, GB, no. 13, 1998, pages 1395 - 1396, XP002102060, ISSN: 1359-7345
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