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Handbook of Green Chemistry

Volume 7
Green Synthesis

Edited by

Chao-Jun Li

Wiley Logo

About the Editors

Series Editor

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Paul T. Anastas joined Yale University as Professor and serves as the Director of the Center for Green Chemistry and Green Engineering there. From 2004–2006, Paul was the Director of the Green Chemistry Institute in Washington, D.C. Until June 2004 he served as Assistant Director for Environment at the White House Office of Science and Technology Policy where his responsibilities included a wide range of environmental science issues including furthering international public-private cooperation in areas of Science for Sustainability such as Green Chemistry. In 1991, he established the industry-governmentuniversity partnership Green Chemistry Program, which was expanded to include basic research, and the Presidential Green Chemistry Challenge Awards. He has published and edited several books in the field of Green Chemistry and developed the 12 Principles of Green Chemistry.

Volume Editor

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Chao-Jun Li (FRSC, UK) received his PhD at McGill University (1992) and was an NSERC Postdoctoral Fellow at Stanford University (1992–1994). He was an Assistant Professor (1994), Associate Professor (1998) and Full Professor (2000–2003) at Tulane University, where he received a NSF CAREER Award (1998) in organic synthesis and the 2001 US Presidential Green Chemistry Challenge Award (Academic). In 2003, he became a Canada Research Chair (Tier I) in Organic/Green Chemistry and a Professor of Chemistry at McGill University in Canada. He serves as the Co-Chair of the Canadian Green Chemistry and Engineering Network, the Director of CFI Infrastructure for Green Chemistry and Green Chemicals, and Co-Director the FQRNT Center for Green Chemistry and Catalysis (Quebec). He is the current Associate Editor for Americas for the journal of Green Chemistry (published by the Royal Society of Chemistry). He has been widely recognized as the leader in Green Chemistry for Organic Synthesis in developing innovative and fundamentally new organic reactions that defy conventional reactivities and have high synthetic efficiency.

List of Contributors

Lutz Ackermann

Georg-August-Universität Göttingen

Institut für Organische und Biomolekulare Chemie

Tammannstrasse 2

37077 Göttingen

Germany

Geoffrey R. Akien

City University of Hong Kong

Department of Biology and Chemistry

Kowloon

Hong Kong

Takahiko Akiyama

Gakushuin University

Department of Chemistry

Mejiro 1-5-1, Toshima-ku

171-8588 Tokyo

Japan

John Andraos

CareerChem

504-1129 Don Mills Road

Toronto, ON M3B 2W4

Canada

Arno Behr

Technische Universität Dortmund

Fakultät Bio- und

Chemieingenieurwesen

Lehrstuhl Technische Chemie A

Emil-Figgestrasse 66

44227 Dortmund

Germany

Alex Chu

Metabomics, Inc.

SuZhou

Jiangsu 215600

China

David J.C. Constable

Lockheed Martin

Energy, Environment, Safety and Health

Gaithersburg, MD 20878

USA

Reinhard W. Hoffmann

Philipps-Universität

Fachbereich Chemie

Hans-Meerwein-Strasse

35032 Marburg

Germany

István T. Horváth

City University of Hong Kong

Department of Biology and Chemistry

Kowloon

Hong Kong

Concepción “Conchita” Jiménez-González

GlaxoSmithKline

Operational Sustainability, Sustainability and Environment

Research Triangle Park, NC 27709

USA

Leif Johnen

Technische Universität Dortmund

Fakultät Bio- und

Chemieingenieurwesen

Lehrstuhl Technische Chemie A

Emil-Figgestrasse 66

44227 Dortmund

Germany

Anant R. Kapdi

Georg-August-Universität Göttingen

Institut für Organische und

Biomolekulare Chemie

Tammannstrasse 2

37077 Göttingen

Germany

Sergei I. Kozhushkov

Georg-August-Universität Göttingen

Institut für Organische und

Biomolekulare Chemie

Tammannstrasse 2

37077 Göttingen

Germany

Zhiping Li

Renmin University of China

Department of Chemistry

No.59, Zhong Guan Cun Street

Beijing 100872 China

László Orha

Eötvös University

Institute of Chemistry

Pázmány Péter Sétány 1/A

1117 Budapest

Hungary

Harish K. Potukuchi

Georg-August-Universität Göttingen

Institut für Organische und Biomolekulare Chemie

Tammannstrasse 2

37077 Göttingen

Germany

Seiji Suga

Okayama University

Graduate School of Natural Science and Technology

Division of Chemistry and Biochemistry

3-1-1 Tsushima-naka, Kita-ku

700-8530 Okayama

Japan

Junhua Tao

Metabomics, Inc.

SuZhou

Jiangsu 215600

China

Barry M. Trost

Stanford University

Department of Chemistry

Stanford, CA 94305

USA

Mei-Xiang Wang

The Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education)

Department of Chemistry

Tsinghua University

100084 Beijing

China

Qian Wang

École Polytechnique Fédérale de Lausanne

EPFL-SB-ISIC-LSPN

BCH 5304 (Bât BCH)

1015 Lausanne

Switzerland

Paul Watts

The University of Hull

Department of Chemistry

Cottingham Road

Hull HU6 7RX

UK

Charlotte Wiles

The University of Hull

Department of Chemistry

Cottingham Road

Hull HU6 7RX

UK

and

Chemtrix BV

Burgemeester Lemmensstraat 358

6163JT Geleen

The Netherlands

Jun-ichi Yoshida

Kyoto University

Graduate School of Engineering

Department of Synthetic Chemistry and Biological Chemistry

Nishikyo-ku

615-8510 Kyoto

Japan

Rong Yu

Renmin University of China

Department of Chemistry

No.59, Zhong Guan Cun Street

Beijing 100872

China

Jieping Zhu

École Polytechnique Fédérale de Lausanne

EPFL-SB-ISIC-LSPN

BCH 5304 (Bât BCH)

1015 Lausanne

Switzerland

Preface

Ever since the synthesis of urea by Friedrich Wöhler near two centuries ago, organic synthesis has become the foundation of modern medicines for human health, produced new agrochemicals to boost world food supply, created various synthetic fibers for daily usages, and bestowed a colorful enchantment through synthetic dyes. In spite of these great achievements, the general features of organic syntheses have been, by and large, unchanged over a century?: e.g., non-renewable feedstock, batch reactor, and refluxing. In addition, classical organic syntheses often produce stoichiometric amount of waste, use organic solvents and sometimes dangerous reagents, require extensive protection-deprotection of functional groups, need pre-functionalized starting materials, and involve multi-step operations, which resulted in low efficiency in resource utilization and led to various concerns due to waste generations. While, in the past, the primary goal of organic syntheses is “ to get the target product”, the sustainability of chemical synthesis becomes a more and more important issue. This volume of Green Syntheses illustrated some examples to address this issue ranging from starting materials, reaction design, choice of solvent, energy input, to reactor design. The chapter by Trost describes the general principle of greener synthesis; the chapter by Behr shows examples of using renewable feedstocks for making chemical products; the chapter by Horvath describes the use of alternative solvents for organic synthesis; the chapters by Zhu, Hoffman and Watts describe methods of reducing synthetic steps by running multi-component reactions, avoiding protecting groups, and in flow respectively; the chapters by Ackermann and Li show examples of direct conversion of C–H bonds; the chapters by Varma and Yoshida presents alternative energy input in chemical reactions through light and electricity; the chapters by Tao and Akiyama give examples of using enzymes and organo catalysts for synthetic purposes; and finally the chapter by Andraos uses computation methods to evaluate the relative efficiency of different synthetic routes. We hope that these examples will provide food-for-thought for further innovations in developing greener syntheses.

Montreal, April 2012

C-J Li