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ACS Pharmaceutical Roundtable Green Chemistry Symposium

Schedule: 
Friday, October 4, 2013 (All day)
Location: 
Life Sciences Atrium
Type: 
Symposium

ACS GCI Pharmaceutical Roundtable and Rutgers University
Catalysis in Green Chemistry Symposium
October 4, 2013

8:00 Registration opens, Breakfast
8:50 Welcome/ Introduction
9:00 Searching for Efficient Reactions in Complex Molecular Environments
Professor Scott Miller, Irénée du Pont Professor and Chair of Chemistry, Yale University
9:50 Novel Organoboron Reagents and Reactivities
Professor Gary Molander, Hirschmann-Makineni Professor of Chemistry, University of Pennsylvania
10:40 Morning Break & Poster Session
11:10 Biocatalysis as an enabling tool for drug development
Dr. Greg Hughes, Executive Director, Enabling Technologies, Process Chemistry, Merck
12:00 Lunch
1:20 Base Metal Catalysis for Organic Synthesis: Applications and Opportunities
Professor Paul Chirik, Edward S. Sanford Professor of Chemistry, Princeton University
2:10 C-H Bond Functionalization in Complex Organic Chemistry
Professor Dalibor Sames, Department of Chemistry, Columbia University
3:00 Afternoon Break & Poster Session
3:30 Formation of C-C Bonds via Hydrogenation and Transfer Hydrogenation
Professor Michael Krische, Robert A. Welch Chair in Science, University of Texas at Austin
4:20 Concluding Remarks
4:30 Symposium Reception

 

Abstracts

Professor Scott Miller
Irénée du Pont Professor and Chair of Chemistry
Yale University

Professor Scott Miller

Searching for Efficient Reactions in Complex Molecular Environments

Complex natural products have provided perennial inspiration for the development of synthetic methods, and enzymes have provided an analogous platform for the conception of new catalysts. This lecture will recount an interplay of experiments stimulated by these two major classes of naturally occurring substances. Specifically, the discovery and use of peptides as catalysts for a variety of asymmetric bond formations – on complex molecular scaffolds – will be presented. Likewise, applications of these catalysts to the selective modification of complex molecules, including biologically active natural products, will be described. The impact of these structural alterations on biological activity will be discussed in selected cases. In all cases, a consideration of the efficiency of the catalytic processes, and critically, catalyst identification, will be undertaken.

Professor Gary Molander
Hirschmann-Makineni Professor of Chemistry
University of Pennsylvania

Professor Gary Molander

Novel Organoboron Reagents and Reactivities

Cross-coupling reactions employing boronic acids have revolutionized the pharma, agrochemical, and other industries by providing facile access to structural systems that were previously difficult to synthesize efficiently. Until recently, little effort has been expended toward further development of the most important component of the process – the organoboron reagent itself. Boronic acids, commonly used for Suzuki-Miyaura coupling, are far from ideal. Because of competitive protodeboronation, literature protocols for cross-coupling employ excess boronic acid to insure a complete conversion of the electrophilic component of the reaction.

Alternative routes to boronic acids and their derivatives utilizing various dibora species will be discussed, with an emphasis on the synthesis and use of the more robust organotrifluoroborate reagents. Novel syntheses of a variety of substructural synthons will be outlined, and unique reagents and chemical transformations will be unveiled as well.

Dr. Greg Hughes
Executive Director, Enabling Technologies, Process Chemistry
Merck Research Labs

Dr. Greg Hughes

Biocatalysis as an enabling tool for drug development

The use of enzymes as catalysts is becoming an increasingly important tactic in the production of pharmaceuticals. This presentation will give an overview of the applications of these tools to the development and production of medicines at Merck, with particular emphasis on the use of engineered enzymes. A brief review of the sitagliptin transaminase development efforts will be presented, with the majority of the presentation focusing on subsequent applications which were inspired and enabled by this work.

Professor Paul Chirik
Edward S. Sanford Professor of Chemistry
Princeton University

Professor Paul Chirak

Base Metal Catalysis for Organic Synthesis: Applications and Opportunities

Transition metal catalysis has revolutionized organic synthesis by enabling new transformations with unprecedented selectivity. Often times, these processes rely on precious metals such as ruthenium, rhodium, iridium and platinum. Our group has been exploring more abundant first row transition metals as alternatives in catalysis. Open questions include – “how can the electronic structure of base metals be altered to achieve the reactivity more traditionally associated with heavier transition metals?” and “can the unique electronic structures of base metals be exploited for new transformations?” Our group has utilized redox-active ligands – those that undergo reversible electron transfer with the transition metal to enable two-electron chemistry with reduced iron and cobalt compounds. This approach has produced catalysts with superior activity and selectivity in reactions such as olefin hydrosilylation and hydrogen than established precious metal compounds. More recently we have focused on the discovery of new base metal precursors for high throughput catalyst evaluation. New phosphine-ligated cobalt compounds have been discovered for asymmetric hydrogenation which demonstrate a new electronic structure paradigm in base metal catalysis. My lecture will focus on the application of base metal catalysis to important transformations and highlight the role of electronic structure on function and mechanism.

Professor Dalibor Sames
Department of Chemistry
Columbia University

Professor Dalibor Sames

C-H Bond Functionalization in Complex Organic Chemistry

The possibility of direct and selective introduction of a new functionality or a new C-C bond via C-H bond functionalization has long intrigued organic chemists as it provides new strategic opportunities for the synthesis of complex organic compounds. I will provide an overview of the efforts in our laboratories aimed at development of new chemical reactions and strategic approaches in organic synthesis. Namely, I will discuss the design of catalytic transformations of both sp2 and sp3 C-H bonds (e.g., C-H arylation of saturated heterocycles and heteroarenes, electrophilic C-H/alkene/alkyne coupling triggered by hydride transfer, and hydroarylation of alkenes and alkynes). Recent advances in scope advancement and mechanistic understanding of the palladium-carboxylate catalytic system (for C-H arylation of arenes and heteroarenes), as well as a new catalytic system for C-H oxidation of pharmaceuticals and pharmaceutical-like compounds, will be discussed.

Professor Michael Krische
Robert A. Welch Chair in Science
University of Texas at Austin

Professor Michael Krische

Formation of C-C Bonds via Hydrogenation and Transfer Hydrogenation

Carbon-carbon bond formation is central to the endeavor of chemical synthesis. The largest volume application of homogenous metal catalyzed C-C coupling is alkene hydroformylation - a “C-C bond forming hydrogenation”. Our laboratory is engaged in the first systematic efforts to develop C-C bond forming hydrogenations beyond hydroformylation - processes wherein two or more reactants are hydrogenated to form a single, more complex product.1 Using cationic rhodium and iridium catalysts, we have found that diverse π-unsaturated reactants reductively couple to carbonyl compounds and imines under hydrogenation conditions, offering a byproduct-free alternative to stoichiometric organometallics in a range of classical C=X (X = O, NR) addition processes. This concept is extended further via “C-C bond forming transfer hydrogenation”. In such processes, the exchange of hydrogen between alcohols and unsaturated reactants serves to generate aldehyde-organometal pairs that combine to give products of carbonyl addition or hydrohydroxyalkylation. Direct alcohol CH-functionalization in this manner is again byproduct-free, and avoids discrete redox manipulations often required to convert alcohols to aldehydes. Representative transformations are given below.2,3

  1. For recent reviews on C-C bond forming hydrogenation and transfer hydrogenation, see: (a) Bower, J. F.; Krische, M. J. Top. Organomet. Chem. 2011, 43, 107. (b) Hassan, A.; Krische, M. J. Org. Proc. Res. Devel. 2011, 15, 1236. (c) Moran, J.; Krische, M. J. Pure Appl. Chem. 2012, 84, 1729.
  2. Geary, L. M.; Glasspoole, B. W.; Kim, M. M. Krische, M. J. J. Am. Chem. Soc. 2013, 134, 3796.
  3. Dechert-Schmitt, A.-M. R.; Schmitt, D. C.; Krische, M. J. Angew. Chem. Int. Ed. 2013, 52, 3195.

Professor Michael Krische Structure

 

Catalysis in Green Chemistry Poster Session

  1. Asymmetric Copper Catalyzed Ketone Reductions with Hydrogen Gas: A Greener Alternative to Transition Metal Hydrogenations, Jeremiah Powers, GSK
  2. Iridium (III) Pincer Complexes in Catalytic Aerobic Methane Oxidation, Meng Zhou, Rutgers University
  3. Integrated Routing Strategy to Explore Xenicane Super Family Structure Space, Huan Wang, Rutgers University
  4. Selective Copper(II) Acetate and Potassium Iodide Catalyzed Oxidation of Aminals to Dihydroquinazoline and Quinazolinone Alkaloids, Chenfei Zhao, Rutgers University
  5. Redox-Neutral α-Amination and α-Oxygenation of Amines, Matthew Richers, Rutgers University
  6. Quantifying the value of an ACS GCI Industrial Roundtable, ACS Green Chemistry Institute®
  7. Greener Synthetic Routes for the Preparation of Avagacestat, Thomas Razler, BMS
  8. Divergent Synthesis of Erythromycin Analogs via Allene Oxidation, Libing Yu, Rutgers University
  9. Conjugate-Base-Stabilized Brønsted Acids as Asymmetric Catalysts: Enantioselective Povarov Reactions with Secondary Aromatic Amines, Chang Min, Rutgers University
  10. The International Consortium for Innovation and Quality in Pharmaceutical Development API Leadership Group – Green Chemistry Working Group, Ingrid Mergelsberg, Merck
  11. Enabling Green Chemistry & Engineering in the Pharmaceutical Industry, ACS GCI Pharmaceutical Roundtable
  12. Enantioselective Base Metal-Catalyzed [2+2]-Cycloadditions, Valerie Schmidt, Princeton University
  13. Mechanisms of Fe and Co-Catalyzed Olefin Hydrosilylation Reactions, Tianning Diao, Princeton University
  14. The Pfizer Green Journey, A Decade of Green Chemistry in the Pharmaceutical Industry, Juan Colberg, Pfizer
  15. Evolution of the GSK Green Reagent Selection Guides, Leanna Shuster, GSK
  16. Cobalt Catalysis for Enantioselective Alkene Hydrogenation, Max Friedfeld, Princeton University
  17. Binaphtholate and Octahydro Binaphtholate Rare-Earth Metal Catalysts for the Asymmetric Hydroamination of Alkenes, Hiep Nguyen, Rutgers University
  18. Green Route to a CGRP Antagonist Employing Three Stereoselective Catalytic Transformations, Collin Chan, BMS
  19. Spirodiexpoxide Based Strategy Towards Total Synthesis of PTX-4, Da Xu, Rutgers University
  20. Redox-Neutral α-Arylation and α,β-Difunctionalization of Amines, Weijie Chen, Rutgers University
  21. Mechanistic Studies of Asymmetric Hydrogenation Catalyzed by Bis(imino)pyridine Cobalt Complexes, Neil Palmer, Princeton University
  22. Base Metal-Catalyzed Hydroboration of Alkenes, Jennifer Obligacion, Princeton University
  23. Atom-Economic C-O Bond Cleavage of Ethers via Iridium Catalysis, Michael Haibach, Rutgers University
  24. Safe and Efficient GMP Manufacture by Application of a Continuous Flow Ozonolysis Followed by Pinnick Oxidation, John Tucker, Amgen
  25. Development of Anion Binding Approach in Asymmetric Catalysis: Application to the Kinetic Resolution of Amines, Nisha Mittal, Rutgers University
  26. Green Chemistry in Chemical Development at BMS, Matthew Hickey, BMS
  27. Redox-Neutral alfa-Cyanation of Amines, Longle Ma, Rutgers University

 

Rutgers Catalysis and Sustainability

 

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The Rutgers Catalysis Research Center (RCRC) supports initiatives by the Rutgers Institute for Materials, Devices, and Nanotechnology (IAMDN) and the Rutgers Energy Institute (REI) and many faculty members in multiple departments around Rutgers who have common research interests in catalysis research. The center consists of researchers from the Departments of Chemistry, Physics, Chemical Engineering, Materials Science, Biological Sciences, Biochemistry, the Laboratory for Surface Modification (LSM), REI, IAMDN, etc.

The Rutgers Catalysis Research Center’s mission is to develop novel homogeneous and heterogeneous catalysts, photocatalysts, biocatalysts, and nanocatalysts that enable greener and energy-efficient routes for the productions of various fine chemicals, pharmaceuticals, commodity chemicals, biofuels, plastics and synthetic materials. Researchers in the center also study fundamental surface science, theoretical aspects of catalysts and catalysis, and investigate catalyst structures and their structure-activity relationships. The center catalyzes mutual interactions and interdisciplinary collaborations among many researchers throughout the greater Rutgers community. Members of the RCRC also actively cooperate and form partnerships with local members of catalysis societies such as the ACS GCI Pharmaceutical Roundtable and the rich catalysis intensive chemical industries in and around New Jersey.

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Rutgers University is a leader in sustainability. One example is the Rutgers University Seven Acre Solar Farm. This facility is one of the largest renewable energy systems on a single campus in the United States. The 1.4 megawatt solar farm generates approximately 11 percent of the electrical demand of the Livingston Campus, reduces the university's carbon dioxide emissions by more than 1,300 tons per year and saves Rutgers tens of thousands of dollars per year.

Rutgers University is also an award-winning, nationally recognized leader in recycling. Over 67% of our waste is diverted from landfills! Please look for recycling opportunities at the symposium.

 

ACS GCI Pharmaceutical Roundtable

 

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The American Chemical Society Green Chemistry Institute® Pharmaceutical Roundtable formed in 2005. Its mission is to catalyze the implementation of green chemistry and green engineering in the pharmaceutical industry globally.

The activities of the Roundtable reflect the joint belief that the pursuit of green chemistry and green engineering is imperative for a sustainable business and world environment. The Roundtable aims to achieve its mission through 4 strategic priorities:

  • informing & influencing the research agenda
  • developing tools for innovation
  • educating leaders
  • collaborating globally

The roundtable is currently made up of 12 globally leading pharmaceutical companies and 3 associate members.

 

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Directions/Map

 

Parking

Visitors may park in Lots 54, 54A & 51A without permits. Event Parking signs will be place at Lots 54 & 54A. Special event parking and special event permits are only for visitors to the University which does not include free metered parking. Faculty, Staff, and Students must park only in lots they are authorized to park in.

 

Thank you to our Symposium Sponsors!

Sponsors

 

Acknowledgments

  • Ken Budrow, Rutgers Catering
  • Karen Fowler, Rutgers Chemistry
  • Stephen Kujan, Rutgers web-design
  • Lindsay Reiff, posters, program

Rutgers, The State University of New Jersey