Department of Chemistry
Indian Institute of Technology Delhi

Water: An Ideal Medium for Chemocatalysis

Prof. Sachin Handa

Department of Chemistry, University of Louisville

Louisville, KY, USA

Date: January 10th 2020 (Friday)
Time: 4:00 PM
Venue: Committee Room (MS710), Department of Chemistry, IIT Delhi

Abstract: If appropriately used, water is arguably the most sustainable and green solvent for conducting organic synthesis.1,2 Nevertheless, misperceptions that the use of water as a solvent in synthesis ultimately leads to an increase in waste generation and that water recycling is difficult continue to hinder its widespread adoption. As evinced by the promulgation of solvent selection guides such as Pfizer’s and Merck’s,3-5 which designates water as the most preferred solvent, attitudes are increasingly changing, but water has yet to attain the popularity it deserves. It is an ideal solvent for chemist safety, process safety, and environmental safety. Contributions from our group and others6-13 have set the foundation to explore chemistry in water for highly selective reaction pathways, especially for industrial applications. To mimic DMF, DMAc, NMP, our group rationally developed an environmentally benign proline-based amphiphile, PS-750-M, that when dissolved in water instantaneously forms nanomicelles with increased inner polarity, distinguishing it from other well-established amphiphiles.12,13 Although transformations requiring DMF, DMAc, and NMP can be achieved with the use of PS-750-M in water, yet substantial number of catalytic transformations heavily rely on rare or precious metal-based catalysts, expensive and non-recyclable ligands, or specialized starting materials requiring labor- and cost-intensive preparation. Often, issues with reproducibility, purity, and selectivity arise at multi-gram scale. In addressing these issues, we have developed inexpensive and environmentally benign nanotechnology, which is sustainable, affordable, and highly reproducible with markedly improved activity, selectivity, and scalability. In particular, the rational design of nanocatalyst, photoactive polymer catalyst,14 and amphiphile for selective reaction pathways will be discussed. Our focus will be on the problematic transformations, which are heavily used by the pharmaceutical industry.
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    References: (1) Breslow, R. Handbook of Green Chemistry. March 2010, 15, pp 1–29; (2) Chang, C.-R.; Huang, Z.-Q.; Li, J. The Promotional Role of Water in Heterogeneous Catalysis: Mechanism Insights from Computational Modeling. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2016, 6, 679; (3) Alfonsi, K.; Colberg, J.; Dunn, P. J.; Fevig, T.; Jennings, S.; Johnson, T. A.; Kleine, H. P.; Knight, C.; Nagy, M. A.; Perry, D. A.; Stefaniak, M. Green Chem. 2008, 10, 31; (4) Prat, D.; Hayler, J.; Wells, A. Green Chem. 2014, 16, 4546; (5) Byrne, F. P.; Jin, S.; Paggiola, G.; Petchey, T. H. M.; Clark, J. H.; Farmer, T. J.; Hunt, A. J.; Robert McElroy, C.; Sherwood, J. Sustain. Chem. Process. 2016, 4, 7; (6) Bihani, M.; Bora, P. P.; Nachtegaal, M.; Jasinski, J. B.; Plummer, S.; Gallou, F.; Handa, S. ACS Catal. 2019, 9, 7520; (7) Ansari, T. N.; Taussat, A.; Clark, A. H.; Nachtegaal, M.; Plummer, S.; Gallou, F.; Handa, S. ACS Catal. 2019, 11, 10389; (8) Brals, J.; Smith, J. D.; Ibrahim, F.; Gallou, F.; Handa, S. ACS Catal. 2017, 7, 7245; (9) Smith, J. D.; Ansari, T. N.; Andersson, M. P.; Yadagiri, D.; Ibrahim, F.; Liang, S.; Hammond, G. B.; Gallou, F.; Handa, S. Green Chem. 2018, 20, 1784; (10) Bora, P. P.; Bihani, M.; Plummer, S.; Gallou, F.; Handa, S. ChemSusChem 2019, 12, 3037; (11) Handa, S.; Wang, Y.; Gallou, F.; Lipshutz, B. H. Science 2015, 349, 1087; (12) Lipshutz, B. H.; Ghorai, S.; Abela, A. R.; Moser, R.; Nishikata, T.; Duplais, C.; Krasovskiy, A.; Gaston, R. D.; Gadwood, R. C. J. Org. Chem. 2011, 76, 4379; (13) Klumphu, P.; Lipshutz, B. H. J. Org. Chem. 2014, 79, 888; (14) Smith, J. D.; Jamhawi, A. M.; Je, J.; Advincula, R.; Gallou, F.; Liu, J.; Handa, S. Nat. Commun. 2019, 10, 1837.

    All are cordially invited to attend.
    Convener (Seminar)