A Scale-Transparent Reaction Calorimetric Assay for Rapid Catalyst Selection

Advanced Synthesis and Catalysis

Volumn 343, Issue 2, 2001, Pages 207-214

  Le Bars, Joel ^a   Häußner, Thomas ^b   Lang, Jutta ^b   Pfaltz, Andreas ^c   Blackmond, Donna G ^a  

^a UNIVERSITY OF HULL   (United Kingdom)

^b EVONIK INDUSTRIES AG   (Germany)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Asymmetric catalysis; Catalyst screening; Hydrogenation; Kinetics; Reaction calorimety

Indexed keywords

EID: 0009877219     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010226)343:2<207::AID-ADSC207>3.0.CO;2-3     Document Type: Review

References (22)

1. For recent reviews, see: (a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2495; (b) R. H. Crabtree, Chem. Commun. 1999, 1611; (c) P. P. Pescarmona, J. C. van der Waal, I. E. Maxwell, T. Maschmeyer, Catal. Lett. 1999, 63, 1; (d) T. Bein, Angew. Chem. Int. Ed. 1999, 38, 323.
2. For recent reviews, see: (a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2495; (b) R. H. Crabtree, Chem. Commun. 1999, 1611; (c) P. P. Pescarmona, J. C. van der Waal, I. E. Maxwell, T. Maschmeyer, Catal. Lett. 1999, 63, 1; (d) T. Bein, Angew. Chem. Int. Ed. 1999, 38, 323.
3. For recent reviews, see: (a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2495; (b) R. H. Crabtree, Chem. Commun. 1999, 1611; (c) P. P. Pescarmona, J. C. van der Waal, I. E. Maxwell, T. Maschmeyer, Catal. Lett. 1999, 63, 1; (d) T. Bein, Angew. Chem. Int. Ed. 1999, 38, 323.
4. For recent reviews, see: (a) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. Int. Ed. 1999, 38, 2495; (b) R. H. Crabtree, Chem. Commun. 1999, 1611; (c) P. P. Pescarmona, J. C. van der Waal, I. E. Maxwell, T. Maschmeyer, Catal. Lett. 1999, 63, 1; (d) T. Bein, Angew. Chem. Int. Ed. 1999, 38, 323.
5. [1d] for general methods; for thermal detection methods for liquid-phase reactions in particular see: (a) M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. Int. Ed. 1998, 37, 2647; (b) M. T. Reetz, M. H. Becker, M. Liebl, A. Furstner, Angew. Chem. Int. Ed. 2000, 39, 1236; (c) S. J. Taylor, J. P. Morken, Science, 1998, 280, 267.
6. [1d] for general methods; for thermal detection methods for liquid-phase reactions in particular see: (a) M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. Int. Ed. 1998, 37, 2647; (b) M. T. Reetz, M. H. Becker, M. Liebl, A. Furstner, Angew. Chem. Int. Ed. 2000, 39, 1236; (c) S. J. Taylor, J. P. Morken, Science, 1998, 280, 267.
7. [1d] for general methods; for thermal detection methods for liquid-phase reactions in particular see: (a) M. T. Reetz, M. H. Becker, K. M. Kuhling, A. Holzwarth, Angew. Chem. Int. Ed. 1998, 37, 2647; (b) M. T. Reetz, M. H. Becker, M. Liebl, A. Furstner, Angew. Chem. Int. Ed. 2000, 39, 1236; (c) S. J. Taylor, J. P. Morken, Science, 1998, 280, 267.
8. (a) Y. Sun, J. Wang, C. LeBlond, J. Laquidara, J. R. Sowa, Jr., D. G. Blackmond, J. Am. Chem. Soc. 1995, 117, 12647;
9. (b) Y. Sun, J. Wang, C. LeBlond, J. Laquidara, J. R. Sowa, Jr., D. G. Blackmond, J. Organomet. Chem. 1997, 548, 65.
10. Recent research has compared the efficiency of liquid-liquid mixing in microreactors and conventional scale reactors: W. Ehrfeld, K. Golbig, V. Hessel, H. Löwe, T. Richter, Ind. & Eng. Chem. Res. 1999, 38, 1075.
11. W. Regenass, ACS Symp. Ser. 1978, 65, 37-42 .
12. Y. Sun, C. LeBlond, J. Wang, A. Forman, R. Larsen, C. Orella, D. G. Blackmond, Thermochim. Acta 1996, 289, 189.
13. (a) European Patent, EP 0967015;
14. (b) J. J. A. Perea, M. Lotz, P. Knochel, Tetrahedron Asymmetry 1999, 10, 375.
15. The approximation of using an initial rate or an average rate will be a good one when the substrate is present in large excess.
16. The processes of dynamic binding-dissociation of ligands or ligand exchange in homogeneous catalytic systems do not in themselves preclude use of the method if the ligands are not used in excess, the same metal is employed in all catalyst samples, and the ratio of catalytic metal to ligand is the same for each catalyst tested in a series.
17. The term "steady-state" is taken in the context of a batch or semi-batch reaction to mean a steady-state concentration of catalytic species within the reaction network (subsequent to any induction periods due to transformation of a catalyst precursor species).
18. i,meas) a given injection may be used to calculate the enantioselectivity achieved by a given catalyst during a given reaction time. Because the enantioselectivity of the mixture changes as a function of time, this is an approximate calculation which may be expected to hold over short conversion intervals. (Equation Presented)
19. W. S. Knowles, Acc. Chem. Res. 1983, 16, 106.
20. H. B. Kagan, in Asymmetric Synthesis, Vol. 5: Chiral Catalysis (Ed.: J. D. Morrison), Academic Press, New York, Ch. 1.
21. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York, Ch. 2.
22. J. Le Bars, U. Specht, J. S. Bradley, D. G. Blackmond, Langmuir 1999, 17, 7621.