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Aldrichimica Acta 48.1 VOL. 48, NO. 1 • 2015 GREEN CHEMISTRY ISSUE • B. H. LIPSHUTZ, GUEST EDITOR CONTRIBUTORS TO THIS ISSUE Anastas • Constable • Gallou and Hamann • Gladysz • Jessop • Koenig • Krische • Lipshutz • Ritter • Stahl • Tucker • Warner ADDITIONAL ONLINE CONTRIBUTORS Rogers • Sheldon TABLE OF CONTENTS Paul T. Anastas: Green Chemistry Next: Moving from Evolutionary Philip G. Jessop: Switchable Solvents as Media for Synthesis to Revolutionary . .3 and Separations . 18 Stephen K. Ritter: Taking a Measure of Green Success . 5 Stefan G. Koenig*, Marian C. Bryan, and Kristi L. Budzinski: David J. C. Constable: Moving Toward a Green Chemistry and The Leading Edge of Green Chemistry at Genentech . .22 Engineering Design Ethic . .7 Bruce H. Lipshutz* and Subir Ghorai: Green Chemistry in the Kelsey C. Miles and Shannon S. Stahl*: Practical Aerobic Alcohol Introductory Organic Laboratory . .23 Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems. .8 Tathagata Mukherjee and John A. Gladysz*: Fluorous Chemistry Fabrice Gallou and Lawrence G. Hamann: Toward a Sustainability Meets Green Chemistry: A Concise Primer. 25 Mindset in the Practice of Pharmaceutical Chemistry—from John C. Warner: Where We Should Focus Green Chemistry Efforts . 29 Early Discovery to Manufacturing . .12 Inji Shin, T. Patrick Montgomery, and Michael J. Krische*: Additional Online Contributors Catalytic C–C Bond Formation and the Hendricksonian Ideal: Atom- and Steven P. Kelley and Robin D. Rogers*: A Practical Overview of Redox-Economy, Stereo- and Site-Selectivity . 15 Organic Synthesis in Ionic Liquids . Aldrich.com/acta John L. Tucker: Pharmaceutical Green Chemistry at Amgen: Roger A. Sheldon: Biocatalysis and Biomass Conversion Seeing with New Eyes . 16 in Ionic Liquids . Aldrich.com/acta Choose the “greener” alternative Aldrichimica Acta—Three “Green” Options Receive timely, topical reviews by leaders in chemical synthesis and reduce paper waste. All options are complimentary. • Download to your iPad® • Receive your subscription via email • Review issues online You can also view the previous 47 years of the Acta via our online archive. Switch to a “greener” Acta; visit Aldrich.com/acta iPad is a registered trademark of Apple Inc. 82375-a 1 VOL. 48, NO. 1 • 2015 Aldrich Chemical Co. LLC. “PLEASE BOTHER US.” 6000 N. Teutonia Ave. Milwaukee, WI 53209, USA Dear Fellow Chemists, Professor Bruce H. Lipshutz and co-workers To Place Orders at UC Santa Barbara have developed three Telephone 800-325-3010 (USA) generations of surfactants (PTS, TPGS, FAX 800-325-5052 (USA) and Nok) that enable transition-metal- or 414-438-2199 catalyzed cross-coupling reactions to be Mail P.O. Box 2060 run in the absence of organic solvents. To further adoption of Milwaukee, WI 53201, USA this technology, Professor Lipshutz has suggested that we offer individual kits containing all materials needed to carry out such Customer & Technical Services transformations: premeasured catalyst, surfactant, and additives—all in a reaction vessel with a Customer Inquiries 800-325-3010 stir bar; just add your substrates! Sigma-Aldrich now offers ten such kits for rapid and convenient Technical Service 800-325-5832 olefin metathesis, as well as C–C, C–B, C–CF3, and C–N bond constructions, in water at room SAFC® 800-244-1173 temperature. Custom Synthesis 800-244-1173 For more information about the technology and our full listing in this area, visit Aldrich.com/ Flavors & Fragrances 800-227-4563 lipshutzkits International 314-771-5765 24-Hour Emergency 314-776-6555 Website sigma-aldrich.com 802271 Suzuki–Miyaura coupling in a box, complete with Lipshutz 1 Kit surfactant in water Email [email protected] 802298 Buchwald–Hartwig amination in a box, complete with Lipshutz 1 Kit General Correspondence surfactant in water Editor: Sharbil J. Firsan, Ph.D. P.O. Box 2060, Milwaukee, WI 53201, USA We welcome your product ideas. Do you need a kit that is not featured on our website or in our [email protected] catalog? Ask Aldrich! For more than 60 years, your research needs and suggestions have shaped the Aldrich product offering. Email your suggestion to [email protected]. Subscriptions Request your FREE subscription to the Aldrichimica Acta, through: iPad® App: Aldrich.com/acta-app Scott Batcheller Web: Aldrich.com/acta Manager Chemistry R&D and Product Management Email: [email protected] Phone: 800-325-3010 (USA) Mail: Attn: Marketing Services Sigma-Aldrich Co. LLC ABOUT OUR COVER 3050 Spruce Street A self-sustaining country estate*—what a fitting subject for St. Louis, MO 63103 the cover of our Acta issue that is dedicated to the topic of Green Chemistry and sustainability in chemical synthesis! Wivenhoe Park, Essex (oil on canvas, 56.1 × 101.2 cm) was painted in 1816 by John Constable (1776–1837), one of the great British landscapists of the 19th century, who is credited with elevating the status of this genre. Constable’s interest in painting started early, but faced initial disapproval from his family; nevertheless, he was able to eventually enroll Detail from Wivenhoe Park, Essex. Photo courtesy National Gallery of Art, Washington, DC. The entire Aldrichimica Acta archive is available at Aldrich.com/acta. at London’s Royal Academy of Art, where he received his formal training. While he never traveled abroad, he had the opportunity to study the works of earlier Aldrichimica Acta (ISSN 0002-5100) is a publication of Aldrich, Dutch and French landscapists. He struggled in his early years to get recognition from the British art a member of the Sigma-Aldrich Group. establishment, which he did not receive until he was into his forties. His artistic influence was greatest after his death and outside of England, particularly in France. ©2015 Sigma-Aldrich Co. LLC. All rights reserved. SIGMA, Constable’s delight in, and profound connection to, nature is obvious in his many paintings of the SAFC, SIGMA-ALDRICH, ALDRICH, and SUPELCO are trademarks countryside of his native Suffolk and other counties in southeast and southwest England. Nowhere is of Sigma-Aldrich Co. LLC, registered in the US and other this more apparent than in this painting with its almost photographic quality. Here, Constable aims to countries. Add Aldrich is a trademark of Sigma-Aldrich Co. capture on canvas a fleeting moment in the life of this idyllic setting and to convey to the viewer the LLC. Aldrich brand products are sold through Sigma-Aldrich, same sensation of balance and harmony between man and nature that it evoked in him. The precise Inc. Purchaser must determine the suitability of the products and crisp brushwork, attention to detail, and the use of billowing, brightly lit clouds to communicate for their particular use. Additional terms and conditions may movement, are characteristic of Constable’s style. apply. Please see product information on the Sigma-Aldrich website at www.sigmaaldrich.com and/or on the reverse side This painting is part of the Widener Collection at the National Gallery of Art, Washington, DC. of the invoice or packing slip. * Wivenhoe Park was a working, self-sustaining country estate when Constable painted it. Can you identify iPad is a registered trademark of Apple Inc. some of the elements in the painting that indicate this sustainability? To find out, visit Aldrich.com/acta481 Try your reaction in water—just add your substrates! Aldrich Chemistry offers a single-use kit for the facile setup of commonly used cross-couplings and other reactions to be done in water via the assistance of Lipshutz Designer Surfactant, TPGS-750-M, on a 0.5 mmol scale. Written protocols are available on our website. Kit Components • Reaction vial with stir bar • Premeasured additives and precatalysts • TPGS-750-M in water • Syringe and septum cap • Fume hood magnet with standard instructions Coming Soon! Reaction Kits • Suzuki–Miyaura Coupling (802271) • Buchwald–Hartwig Amination (802298) • Sonogashira Coupling (802301) • Heck Coupling (802328) • Stille Coupling (802336) • Negishi Coupling (802344) • Miyaura Borylation (802352) • Olefin Metathesis (802360) • Trifluoromethylation (802379) • Amide Coupling (802387) For more information or to order: Aldrich.com/lipshutzkits 82375-b 3 VOL. 48, NO. 1 • 2015 Green Chemistry Next: Moving from Evolutionary to Revolutionary A View from the Co-Author of the 12 Principles of Green Chemistry Paul T. Anastas† Center for Green Chemistry and Green Engineering, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA • Email: [email protected] The Past such as renewable energy, sustainable food production, water purification, Green Chemistry was launched as a field of endeavor in 1991, and has since and pollutant elimination. All of these challenges are important and, in the evolved significantly while remaining true to its bedrock foundations.1 future, Green Chemistry will need to develop approaches that accomplish From the beginning, the field was about inventions and innovations, multiple goals simultaneously. Instead of merely reducing waste, for rather than limitations and restrictions, and has been based on the premise instance, Green Chemistry technologies would convert and utilize the that proactive design is essential and far more desirable than reacting to “waste” material for value-added applications. Examples exist of sewerage problems after they arise.2 Green Chemistry considers as its appropriate bio-solids waste being utilized to generate energy and provide purified scope the entire life cycle of a chemical or material,3 rather than simply water. Other examples
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