High Pressure-a Useful Parameter for Catalysis?

Oliver Reiser

doi:10.4131/jshpreview.8.111

Oliver Reiser

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Keywords: catalysis, organic reaction, cycloaddition, Lewis acid, palladium, Heck-reaction, alkenylation

JOURNAL FREE ACCESS

1998 Volume 8 Issue 2 Pages 111-120

DOI https://doi.org/10.4131/jshpreview.8.111

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Published: May 20, 1998 Received: March 16, 1998 Available on J-STAGE: August 07, 2009 Accepted: - Advance online publication: - Revised: -
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Date of correction: August 07, 2009 Reason for correction: - Correction: CITATION Details: Wrong : [1] B. M. Trost: Angew. Chem 107, 285-307 (1995), "Atomönomische Syntheses - eine Herausforderung in der Organischen Chemie: die Homogenkatalyse als wegweisende Methode".
[2] Leading Reviews: (a) G. Jennec 53, 2669-2695 (1997), "High Pressure and Selectivity in Organic Reactions". (b) J. Jurczak, B. Baranowski: High Pressure Chemical Synthesis; Elsevier: Amsterdam-Oxford-New York-Tokyo, 1989. (c) K. Matsumoto, A. Sera, T. Uchida: Synthesis 1-26 (1985), "Organic Synthesis under High Pressure; I". (d) K. Matsumoto, A. Sera: Synthesis 999-1027 (1985), "Organic Synthesis under High Pressure; II". (e) F. -G. Klämer: Chemie in unserer Zeit, 23, 53-63 (1989), "Chemie unter Hochdruck". (f) W. J. le Noble: Chemie in unserer Zeit, 17, 152-162 (1983), "Der Einfluβ von Druck auf organische Reaktionen in Lösung". (g) O. Reiser: Topics in Catalysis, 5, 105-112 (1998), "Catalysis and High Pressure - a Useful Liaison?!"
[3] F. -G. Klämer: personal communication.
[4] G. Jenner. J. Chem. Soc. Faraday Trans 1, 81, 2437-2460 (1985), "The Pressure Effect on Strained Transition States".
[5] (a) Y. Yamamoto, K. Saito: J. Chem. Soc. Chem Commun. , 1676-1678 (1989), "Intervention of the Boat Transition State in the Allylic Tin-Aldehyde Condensation at High Pressure". (b) Y. Yamamoto, K. Maruyama, K. Matsumoto: J. Chem. Soc. Chem Comun. 489-490 (1983), "Organometallic High Pressure Reactions, Allylation of Aldehydes with Allylic Stannanes under Mild Conditions".
[6] L. F. Tietze, T. Hübsch, E. Voss, M. Buback, W. Trost: J. Am. Chem. Soc. 110, 4065-4066 (1988), "Intermolecular Hetero-Diels-Alder Reactions of Enamino Ketones at High Pressure. The First Significant Pressure-Induced Diastereoselectivity in Organic Transformations".
[7] F. -G. Klämer, B. M. J. Dogan, 0. Enner, W. v. E. Doering, M. P. Cohen: Angew. Chem. 98, 109-111 (1986), "Mechanismus der thermischen 1, 3-Cyclohexadien-Dimerisierung: Eine nicht konzertierte Diets-Alder Reaktion zum exo-[4+2]-Addukt sowie eine neuartige [6+4]-En-Reaktion".
[8] A. Golebiowski, J. Jurczak: Tetrahdron: 47, 1037-1044 (1991), "High Pressure [4+2] Cycloaddition of 1-Methoxy-1, 3-butadiene to N, O-Protected D-Threoninals and D-Allo-Threoninals. "
[9] A. Golebiowski, J. Jurczak: Tetrahedron, 47, 1045-1052 (1991), "The Cyclocondensation Reaction of 1-Benzoyloxy-2-tert-butyl-dimethylsilyloxy-4-methoxy-1, 3-butadiene with N, O-protected D-Thrtoninals and D-Allo-Threoninals".
[10] N. Katagiri, N. Watanabe, C. Kaneko: Chem. Pharm. Bull. , 38, 69-72 (1990), "Synthesis of Nucleosides and Related Compounds. XIV. Dies-Alder Reaction of Di-l-menthyl Acetoxymethylenemalonate wit Cyclopentadiene: Effects of High-Pressure and Catalysts upon Asymmetric Induction".
[11] L. F. Tietze C. Ott, K. Gerke, M. Buback: Angew. Chem. 105, 1536-1538 (1993), "Steigerung der Enantio-selektivität chemischer Reaktionen in Gegenwart chiraler Lewis-Säuren durch hohen Druck. "
[12] L. F. Tietze, C. Ott, U. Frey: Liebigs Ann. , 63-67 (1996), "Enantioselective Diels-Alder Reactions NMR Spectroscopy of a Chiral Titanium Lewis Acid under High Pressure".
[13] R. W. M. Aben, E. P. Limburg, H. W. Scheeren: High Pressure Research, 11, 167-170 (1992), "A One Step Synthesis of Novel 4-Alkoxy-β-Lactams by High Pressure Promoted [2+2] Cycloadditions of Enol Ethers and Isocyanates Derived from Amino Acids".
[14] H. Kotsuki, M. Teraguchi, N. Shimomoto, M. Ochi, Tetrahedron Lett. , 37, 3727-3730 (1996), "Ytterbium (III) Triflouromethanesulfonate Catalyzed High Pressure Reaction of Epoxides with Indole. An Enantiosetective Synthesis of (+) -Diolmycin A2".
[15] (a) M. M. Midland, J. L McLoughlin: J. Org. Chem. 49, 1317 (1984), "Asymmetric Synthesis of Prochiral Ketones with B-3-Pinanyl-9-borabicyclo[3. 3. 1]nonane in Efficien-cies approaching 100%. Simultaneous Rate Enhancement and Side Reaction Supression via the Use of Elevated Pressure. ". (b) M. M. Midland, J. I. McLoughlin: J. Org. Cham. 54, 159 (1989), "Asymmetric Reductions of Prochiral Ketones with B-3-Pinanyl-9-borabicyclo[3. 3. 1]-nonane (Alpine-Borane) at Elevated Pressures".
[16] T. Sugihara, M. Takebayashi, C. Kaneko: Tetrahedron Lett. 36, 5547-5550 (1995), "Effects of High Pressure on the Heck Reaction. Is it Possible to Control Dehydro-palladatnn of Alkylpalladium Intermediates having β-Hydrogens?"
[17] R. v. Eldik, T. Asano, W. J. l. Noble: Chem. Rev. 89, 549-688 (1989), "Activation and Reaction Volumes in Solution. 2".
[18] S. Hillers, O. Reiser: J. Chem. Soc. Chem. Commun. 2197-2198 (1996), "First Detemnination of the Rate Acceleration of a Palladium Catalyzed Coupling Reaction by High Pressure".
[19] S. Hillers, S. Saraton, O. Reiser: J. Am. Chem. Soc. 118, 2077-2078 (1996), "A Dramatical Increase of Turn Over Cycles in Palladium-Catalyzed Coupling Reactions Using High Pressure Conditions".
[20] (a) R. C. Larodc, W. H. Gong: J. Org. Chem. 55, 407-408 (1990), "Palladium-catalyzed synthesis of turns-2, 5-diaryltetrahydrofurans, potent platelet activating factor antagonists. " (b) R. C. Larodc. , W. H. Gong: J. Org. Chem 54, 2047 (1989), "Palladium-catalyzed internnolecular vinylation of cyclic alkenes".
[21] (a) F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, E. Nishioka, K. Yanagi, K. Moriguchi: Organometallics, 12, 4188 (1993), "Palladium-Catalyzed Asymmetric Aryhtion of 2, 3-Dihydrofuran with Phenyl Triflate - A Novel Asymmetric Catalysis Involving a Kinetic Resolution Process". (b) F. Ozawa, Y. Kobatake: T. Hayashi, Tetrahedron Lett. , 34, 2505-2508 (1993), "Palladium-Catalyzed Asymmetric Alkenylation of Cyclic Olefms".
[22] (a) S. Hillers, A. Niklaus, O. Reiser: J. Org. Chem. 58, 3169-3171 (1993), "Ozonolysis of Cyclic Enol Ethers - An Efficient Strategy to Aldol and Homoaldol Compounds". (b) S. Hillers, O. Reiser: Synlett 153-154 (1995), "Palladium-Catalyzed Arybtion and Vinylation of 4-Alkyl Substituted 2, 3-Dihydrofurans: A Catalytic Sequence to Anti-Aldol Compounds". (c) C. Bubert, J. Voigt, S. Biasetton, O. Reiser: 675-677 (1994), "A New Approach to β- and γ-Amino Esters and Amino Aldehydes by Regioselective Ozonolysis of 2, 3- Dihydropyrroles and 1, 2, 3, 4-Tetrahydropyridines".
[23] A. Suzuki, Pure Appl. Chem, 63, 419-422 (1991), "Synthetic studies via the cross-coupling reaction of organoboron derivatives with organic halides".
[24] A. Mengel, C. Frost, J. Williams, O. Reiser: unpublished results.
[25] K. Voigt, U. Schick, F. E. Meyer, A, d. Meijere: Synlett, 189-190 (1994), "Rate Enhancement of Palladium-Catalyzed Alkene to Alkenyl and Aryl Halide Couplings under High Pressure".
[26] M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai: Tetrahedron Lett. , 25, 2183-2186 (1984), "Horner-Wadsworth-Emmons Reaction: Use of Lithium Chloride and an Amine for Base-sensitive Compounds".
[27] S. Hillers, A. Mengel, K. Bodmann, O. Reiser: in Proc. the XVI AIRAPT Intl. Conf on High Pressure Sci. Tech. , Kyoto 1997, in print, "The Influence of High Pressure on Palladium-Catalyzed Coupling Reactions".
[28] M. Moreno-Manas, M. Perez, R. Pleixats: Tetrahedron Lett. , 41, 7449 (1996), "Stereospecific Preparation of Ethyl (E) and (Z) -3-Aryl-3-Phenylpropenoates by Heck Reaction".
[29] S. Hillers, O. Reiser: Tetrahedron Lett. 34, 5265 (1993), "Palladium Catalyzed Coupling Reactions of 2, 3-dihydrofuran Using High Pressure Conditions".
[30] B. M. Trost, J. R. Parquette, A. L. Marquart, 117, 3284-3285 (1995), "Effect of High Pressure on a Transition-Metal-Catalyzed Cycloaddition".

Right : [1] B. M. Trost: Angew. Chem 107, 285-307 (1995), "Atomönomische Syntheses - eine Herausforderung in der Organischen Chemie: die Homogenkatalyse als wegweisende Methode".
[2] Leading Reviews: (a) G. Jennec 53, 2669-2695 (1997), "High Pressure and Selectivity in Organic Reactions". (b) J. Jurczak, B. Baranowski: High Pressure Chemical Synthesis; Elsevier: Amsterdam-Oxford-New York-Tokyo, 1989. (c) K. Matsumoto, A. Sera, T. Uchida: Synthesis 1-26 (1985), "Organic Synthesis under High Pressure; I". (d) K. Matsumoto, A. Sera: Synthesis 999-1027 (1985), "Organic Synthesis under High Pressure; II". (e) F. -G. Klämer: Chemie in unserer Zeit, 23, 53-63 (1989), "Chemie unter Hochdruck". (f) W. J. le Noble: Chemie in unserer Zeit, 17, 152-162 (1983), "Der Einfluβ von Druck auf organische Reaktionen in Lösung". (g) O. Reiser: Topics in Catalysis, 5, 105-112 (1998), "Catalysis and High Pressure - a Useful Liaison?!"
[3] F. -G. Klämer: personal communication.
[4] G. Jenner. J. Chem. Soc. Faraday Trans 1, 81, 2437-2460 (1985), "The Pressure Effect on Strained Transition States".
[5] (a) Y. Yamamoto, K. Saito: J. Chem. Soc. Chem Commun. , 1676-1678 (1989), "Intervention of the Boat Transition State in the Allylic Tin-Aldehyde Condensation at High Pressure". (b) Y. Yamamoto, K. Maruyama, K. Matsumoto: J. Chem. Soc. Chem Comun. 489-490 (1983), "Organometallic High Pressure Reactions, Allylation of Aldehydes with Allylic Stannanes under Mild Conditions".
[6] L. F. Tietze, T. Hübsch, E. Voss, M. Buback, W. Trost: J. Am. Chem. Soc. 110, 4065-4066 (1988), "Intermolecular Hetero-Diels-Alder Reactions of Enamino Ketones at High Pressure. The First Significant Pressure-Induced Diastereoselectivity in Organic Transformations".
[7] F. -G. Klämer, B. M. J. Dogan, 0. Enner, W. v. E. Doering, M. P. Cohen: Angew. Chem. 98, 109-111 (1986), "Mechanismus der thermischen 1, 3-Cyclohexadien-Dimerisierung: Eine nicht konzertierte Diets-Alder Reaktion zum exo-[4+2]-Addukt sowie eine neuartige [6+4]-En-Reaktion".
[8] A. Golebiowski, J. Jurczak: Tetrahdron: 47, 1037-1044 (1991), "High Pressure [4+2] Cycloaddition of 1-Methoxy-1, 3-butadiene to N, O-Protected D-Threoninals and D-Allo-Threoninals. "
[9] A. Golebiowski, J. Jurczak: Tetrahedron, 47, 1045-1052 (1991), "The Cyclocondensation Reaction of 1-Benzoyloxy-2-tert-butyl-dimethylsilyloxy-4-methoxy-1, 3-butadiene with N, O-protected D-Thrtoninals and D-Allo-Threoninals".
[10] N. Katagiri, N. Watanabe, C. Kaneko: Chem. Pharm. Bull. , 38, 69-72 (1990), "Synthesis of Nucleosides and Related Compounds. XIV. Dies-Alder Reaction of Di-l-menthyl Acetoxymethylenemalonate wit Cyclopentadiene: Effects of High-Pressure and Catalysts upon Asymmetric Induction".
[11] L. F. Tietze C. Ott, K. Gerke, M. Buback: Angew. Chem. 105, 1536-1538 (1993), "Steigerung der Enantio-selektivität chemischer Reaktionen in Gegenwart chiraler Lewis-Säuren durch hohen Druck. "
[12] L. F. Tietze, C. Ott, U. Frey: Liebigs Ann. , 63-67 (1996), "Enantioselective Diels-Alder Reactions NMR Spectroscopy of a Chiral Titanium Lewis Acid under High Pressure".
[13] R. W. M. Aben, E. P. Limburg, H. W. Scheeren: High Pressure Research, 11, 167-170 (1992), "A One Step Synthesis of Novel 4-Alkoxy-β-Lactams by High Pressure Promoted [2+2] Cycloadditions of Enol Ethers and Isocyanates Derived from Amino Acids".
[14] H. Kotsuki, M. Teraguchi, N. Shimomoto, M. Ochi, Tetrahedron Lett. , 37, 3727-3730 (1996), "Ytterbium (III) Triflouromethanesulfonate Catalyzed High Pressure Reaction of Epoxides with Indole. An Enantiosetective Synthesis of (+) -Diolmycin A2".
[15] (a) M. M. Midland, J. L McLoughlin: J. Org. Chem. 49, 1317 (1984), "Asymmetric Synthesis of Prochiral Ketones with B-3-Pinanyl-9-borabicyclo[3. 3. 1]nonane in Efficien-cies approaching 100%. Simultaneous Rate Enhancement and Side Reaction Supression via the Use of Elevated Pressure. ". (b) M. M. Midland, J. I. McLoughlin: J. Org. Cham. 54, 159 (1989), "Asymmetric Reductions of Prochiral Ketones with B-3-Pinanyl-9-borabicyclo[3. 3. 1]-nonane (Alpine-Borane) at Elevated Pressures".
[16] T. Sugihara, M. Takebayashi, C. Kaneko: Tetrahedron Lett. 36, 5547-5550 (1995), "Effects of High Pressure on the Heck Reaction. Is it Possible to Control Dehydro-palladatnn of Alkylpalladium Intermediates having β-Hydrogens?"
[17] R. v. Eldik, T. Asano, W. J. l. Noble: Chem. Rev. 89, 549-688 (1989), "Activation and Reaction Volumes in Solution. 2".
[18] S. Hillers, O. Reiser: J. Chem. Soc. Chem. Commun. 2197-2198 (1996), "First Detemnination of the Rate Acceleration of a Palladium Catalyzed Coupling Reaction by High Pressure".
[19] S. Hillers, S. Saraton, O. Reiser: J. Am. Chem. Soc. 118, 2077-2078 (1996), "A Dramatical Increase of Turn Over Cycles in Palladium-Catalyzed Coupling Reactions Using High Pressure Conditions".
[20] (a) R. C. Larodc, W. H. Gong: J. Org. Chem. 55, 407-408 (1990), "Palladium-catalyzed synthesis of turns-2, 5-diaryltetrahydrofurans, potent platelet activating factor antagonists. " (b) R. C. Larodc. , W. H. Gong: J. Org. Chem 54, 2047 (1989), "Palladium-catalyzed internnolecular vinylation of cyclic alkenes".
[21] (a) F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, E. Nishioka, K. Yanagi, K. Moriguchi: Organometallics, 12, 4188 (1993), "Palladium-Catalyzed Asymmetric Aryhtion of 2, 3-Dihydrofuran with Phenyl Triflate - A Novel Asymmetric Catalysis Involving a Kinetic Resolution Process". (b) F. Ozawa, Y. Kobatake: T. Hayashi, Tetrahedron Lett. , 34, 2505-2508 (1993), "Palladium-Catalyzed Asymmetric Alkenylation of Cyclic Olefms".
[22] (a) S. Hillers, A. Niklaus, O. Reiser: J. Org. Chem. 58, 3169-3171 (1993), "Ozonolysis of Cyclic Enol Ethers - An Efficient Strategy to Aldol and Homoaldol Compounds". (b) S. Hillers, O. Reiser: Synlett 153-154 (1995), "Palladium-Catalyzed Arybtion and Vinylation of 4-Alkyl Substituted 2, 3-Dihydrofurans: A Catalytic Sequence to Anti-Aldol Compounds". (c) C. Bubert, J. Voigt, S. Biasetton, O. Reiser: 675-677 (1994), "A New Approach to β- and γ-Amino Esters and Amino Aldehydes by Regioselective Ozonolysis of 2, 3- Dihydropyrroles and 1, 2, 3, 4-Tetrahydropyridines".
[23] A. Suzuki, Pure Appl. Chem, 63, 419-422 (1991), "Synthetic studies via the cross-coupling reaction of organoboron derivatives with organic halides".
[24] A. Mengel, C. Frost, J. Williams, O. Reiser: unpublished results.
[25] K. Voigt, U. Schick, F. E. Meyer, A, d. Meijere: Synlett, 189-190 (1994), "Rate Enhancement of Palladium-Catalyzed Alkene to Alkenyl and Aryl Halide Couplings under High Pressure".
[26] M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai: Tetrahedron Lett. , 25, 2183-2186 (1984), "Horner-Wadsworth-Emmons Reaction: Use of Lithium Chloride and an Amine for Base-sensitive Compounds".
[27] S. Hillers, A. Mengel, K. Bodmann, O. Reiser: in Proc. the XVI AIRAPT Intl. Conf on High Pressure Sci. Tech. , Kyoto 1997, in print, "The Influence of High Pressure on Palladium-Catalyzed Coupling Reactions".
[28] M. Moreno-Manas, M. Perez, R. Pleixats: Tetrahedron Lett. , 41, 7449 (1996), "Stereospecific Preparation of Ethyl (E) and (Z) -3-Aryl-3-Phenylpropenoates by Heck Reaction".
[29] S. Hillers, O. Reiser: Tetrahedron Lett. 34, 5265 (1993), "Palladium Catalyzed Coupling Reactions of 2, 3-dihydrofuran Using High Pressure Conditions".
[30] B. M. Trost, J. R. Parquette, A. L. Marquart, 117, 3284-3285 (1995), "Effect of High Pressure on a Transition-Metal-Catalyzed Cycloaddition".

Abstract

The scope and limitation of high pressure for the catalysis of organic reactions is evaluated. This article focuses on Lewis acid (cycloadditions, epoxide openings, Horner-Wadsworth-Emmons reactions) and palladium catalyzed (Heck-reaction, [3+2] cycloadditions) reactions. Aspects of reactivity (turnover frequencies and turnover rates) as well as selectivity (chemoselectivity, regioselectivity, diastereo- and enantioselectivity) under the influence of pressure will be discussed.

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