Time-resolved IR-thermographic detection and screening of enantioselectivity in catalytic reactions

Angewandte Chemie - International Edition

Volumn 37, Issue 19, 1998, Pages 2647-2650

  Reetz, Manfred T ^a   Becker, Michael H ^a   Kühling, Klaus M ^a   Holzwarth, Arnold ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric catalysis; Biocatalysts; Combinatorial chemistry; Homogeneous catalysis; IR thermographic screening

Indexed keywords

EID: 0032538361     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2647::AID-ANIE2647>3.0.CO;2-I     Document Type: Article

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28. Application of IR cameras in the thermographic detection of chemical processes based on heterogeneous catalysis: a) G. Georgiades, V. A. Self, P. A. Sermon, Angew. Chem. 1987, 99, 1050-1052: Angew. Chem. Int. Ed. Engl. 1987, 26, 1042-1043; b) P. C. Pawlicki, R. A. Schmitz, Chem. Eng. Prog. 1987, 83 (2), 40-45; c) L. Lobban, G. Philippou, D. Luss, J. Phys. Chem. 1989, 93, 733-736; d) F. C. Moates, M. Somani, J. Annamalai, J. T. Richardson, D. Luss, R. C. Willson, Ind. Eng. Chem. Res. 1996, 35, 4801-4803; e) D. E. Bergbreiter, Chemtracts: Org. Chem. 1997, 10, 683-686; f) S. J. Taylor, J. P. Morken, Science 1998, 280, 267-270.
29. Application of IR cameras in the thermographic detection of chemical processes based on heterogeneous catalysis: a) G. Georgiades, V. A. Self, P. A. Sermon, Angew. Chem. 1987, 99, 1050-1052: Angew. Chem. Int. Ed. Engl. 1987, 26, 1042-1043; b) P. C. Pawlicki, R. A. Schmitz, Chem. Eng. Prog. 1987, 83 (2), 40-45; c) L. Lobban, G. Philippou, D. Luss, J. Phys. Chem. 1989, 93, 733-736; d) F. C. Moates, M. Somani, J. Annamalai, J. T. Richardson, D. Luss, R. C. Willson, Ind. Eng. Chem. Res. 1996, 35, 4801-4803; e) D. E. Bergbreiter, Chemtracts: Org. Chem. 1997, 10, 683-686; f) S. J. Taylor, J. P. Morken, Science 1998, 280, 267-270.
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31. Application of IR cameras in the thermographic detection of chemical processes based on heterogeneous catalysis: a) G. Georgiades, V. A. Self, P. A. Sermon, Angew. Chem. 1987, 99, 1050-1052: Angew. Chem. Int. Ed. Engl. 1987, 26, 1042-1043; b) P. C. Pawlicki, R. A. Schmitz, Chem. Eng. Prog. 1987, 83 (2), 40-45; c) L. Lobban, G. Philippou, D. Luss, J. Phys. Chem. 1989, 93, 733-736; d) F. C. Moates, M. Somani, J. Annamalai, J. T. Richardson, D. Luss, R. C. Willson, Ind. Eng. Chem. Res. 1996, 35, 4801-4803; e) D. E. Bergbreiter, Chemtracts: Org. Chem. 1997, 10, 683-686; f) S. J. Taylor, J. P. Morken, Science 1998, 280, 267-270.
32. 2 IR camera (AIM, Heilbronn, Germany) with a PtSi-FPA detector and a germanium lens. This detection system is sensitive to IR radiation in the wavelength range 3-5 μm and to temperature changes of 10-100 mK, depending upon the conditions.
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45. For the catalyst screening in the hydrolysis of epichlorohydrin 3c a mixture of (S,S)-5a, (S,S)-5b, and (S,S)-5c (each 60.0 μmol) in toluene (1.00 mL) and acetic acid (120 μmol, 7.21 mg, 6.86 mL) was stirred in an open flask for 1 h. After removal of the solvent the three residues were dried in vacuum. Each of these activated catalysts (S,S)-5a-c was dissolved in toluene (300 μL) and distributed in three reaction vessels. Epichlorohydrin 3c (1.00 mmol, 92.5 mg, 78.4 mL) was added. As described before the temperature was calibrated in the range of 24-39°C. The reaction was initiated by the addition of water (0.55 equiv, 0.55 mmol, 9.9 μL) at 27°C. Screening was performed similar to the first experiments, except that the detection time was prolonged, averaging 500 recordings in 10 s.
46. For the substrate activity screening the cobalt catalyst (S,S)-5c was activated as described before. Nine aliquots each containing 2.00 μmol of the catalyst in toluene (100 μL) were distributed in the wells of the microtiter plate. The three different epoxides 3a-c in the (R-, (S)-, and rac-form were added to the catalyst, resulting in the arrangement shown in Figure 3. The reaction mixtures contained the epoxides at a concentration of 3.95 M in toluene and a final volume of 253 μL. Detection of the reactions was performed for 10s, resulting in 500 recordings which were averaged.
47. [12, 13]