Sulfur Chemistry PDF
Preview Sulfur Chemistry
Topics in Current Chemistry Collections Xuefeng Jiang Editor Sulfur Chemistry Topics in Current Chemistry Collections Journal Editors Massimo Olivucci, Siena, Italy and Bowling Green, USA Wai-Yeung Wong, Hong Kong, China Series Editors Hagan Bayley, Oxford, UK Greg Hughes, Codexis Inc, USA Christopher A. Hunter, Cambridge, UK Seong-Ju Hwang, Seoul, South Korea Kazuaki Ishihara, Nagoya, Japan Barbara Kirchner, Bonn, Germany Michael J. Krische, Austin, USA Delmar Larsen, Davis, USA Jean-Marie Lehn, Strasbourg, France Rafael Luque, Córdoba, Spain Jay S. Siegel, Tianjin, China Joachim Thiem, Hamburg, Germany Margherita Venturi, Bologna, Italy Chi-Huey Wong, Taipei, Taiwan Henry N.C. Wong, Hong Kong, China Vivian Wing-Wah Yam, Hong Kong, China Chunhua Yan, Beijing, China Shu-Li You, Shanghai, China Aims and Scope The series (cid:84)(cid:111)(cid:112)(cid:105)(cid:99)(cid:115)(cid:32)(cid:105)(cid:110)(cid:32)(cid:67)(cid:117)(cid:114)(cid:114)(cid:101)(cid:110)(cid:116)(cid:32)(cid:67)(cid:104)(cid:101)(cid:109)(cid:105)(cid:115)(cid:116)(cid:114)(cid:121)(cid:32)(cid:67)(cid:111)(cid:108)(cid:108)(cid:101)(cid:99)(cid:116)(cid:105)(cid:111)(cid:110)(cid:115) presents critical reviews from the journal (cid:84)(cid:111)(cid:112)(cid:105)(cid:99)(cid:115)(cid:32)(cid:105)(cid:110)(cid:32)(cid:67)(cid:117)(cid:114)(cid:114)(cid:101)(cid:110)(cid:116)(cid:32)(cid:67)(cid:104)(cid:101)(cid:109)(cid:105)(cid:115)(cid:116)(cid:114)(cid:121) organized in topical volumes. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Moreinformationaboutthisseriesathttp://www.springer.com/series/14181 Xuefeng Jiang Sulfur Chemistry With contributions from Satpal Singh Badsara • R. Sidick Basha • Justin M. Chalker Wei Chen • M. Emin Cinar • Ponnam Devendar • Louisa J. Esdaile Richard S. Glass • Tao Jia • Xuefeng Jiang • Chin‑Fa Lee • Jian Liao Yan Liu • Nicholas A. Lundquist • Nuno Maulide • Lingkui Meng Jérémy Merad • Toshiaki Murai • Thomas J. J. Müller James D. Neuhaus • Jon T. Njardarson • Keisuke Nogi • Rik Oost Shinya Otsuka • Turan Ozturk • Klaus Schaper • Kevin A. Scott Gulsen Turkoglu • Qian Wan • Ming Wang • Min Wang Max J. H. Worthington • Guang-Fu Yang • Hideki Yorimitsu Jing Zeng • Xiang Zhao Editor Xuefeng Jiang School of Chemistry & Molecular Engineering East China Normal University Shanghai, China Partly previously published in Top Curr Chem (Z) Volume 375 (2017); Top Curr Chem (Z) Volume 376 (2018); Topics in Current Chemistry Volume 377 (2019). ISSN 2367-4067 Topics in Current Chemistry Collections I SBN 978-3-030-25597-8 © Springer Nature Switzerland AG 2019 The chapter “Sulfur‑Based Ylides in Transition‑Metal‑CatalysedProcesses” is licensed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/). For further details see license information in the chapters. This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors, and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. The publisher remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. This Springer imprint is published by the registered company Springer Nature Switzerland AG The registered company address is: Gewerbestrasse 11, 6330 Cham, Switzerland Contents Preface ................................................................................................................. vii Analysis of US FDA‑Approved Drugs Containing Sulfur Atoms ................. 1 Kevin A. Scott and Jon T. Njardarson: Top Curr Chem (Z) 2018, 376:5 (22, January 2018) https://doi.org/10.1007/s41061-018-0184-5 Sulfur-Containing Agrochemicals .................................................................... 35 Ponnam Devendar and Guang-Fu Yang: Top Curr Chem (Z) 2017, 375:82 (9, October 2017) https://doi.org/10.1007/s41061-017-0169-9 Thiophene-Based Organic Semiconductors .................................................... 79 Gulsen Turkoglu, M. Emin Cinar and Turan Ozturk: Top Curr Chem (Z) 2017, 375:84 (24, October 2017) https://doi.org/10.1007/s41061-017-0174-z Synthesis and Applications of Polymers Made by Inverse Vulcanization ... 125 Justin M. Chalker, Max J. H. Worthington, Nicholas A. Lundquist and Louisa J. Esdaile: Topics in Current Chemistry 2019, 377:16 (20, May 2019) https://doi.org/10.1007/s41061-019-0242-7 Engineered C–S Bond Construction ................................................................ 153 Chin‑Fa Lee, R. Sidick Basha and Satpal Singh Badsara: Top Curr Chem (Z) 2018, 376:25 (4, June 2018) https://doi.org/ 10.1007/s41061-018-0203-6 C–S Bond Activation ......................................................................................... 199 Shinya Otsuka, Keisuke Nogi and Hideki Yorimitsu: Top Curr Chem (Z) 2018, 376:13 (10, April 2018) https://doi.org/ 10.1007/s41061-018-0190-7 The Construction and Application of C=S Bonds .......................................... 239 Toshiaki Murai: Topics in Current Chemistry 2018, 376:31 (10, July 2018) https://doi.org/10.1007/s41061-018-0209-0 v vi Contents Thiophene Syntheses by Ring Forming Multicomponent Reactions ............ 261 Klaus Schaper and Thomas J. J. Müller: Topics in Current Chemistry 2018, 376:38 (17, September 2018) https://doi.org/10.1007/ s41061-018-0216-1 Sulfur–Sulfur Bond Construction .................................................................... 285 Ming Wang and Xuefeng Jiang: Top Curr Chem (Z) 2018, 376:14 (10, April 2018) https://doi.org/10.1007/s41061-018-0192-5 Sulfur Radicals and Their Application ............................................................ 325 Richard S. Glass: Top Curr Chem (Z) 2018, 376:22 (9, May 2018) https://doi.org/10.1007/s41061-018-0197-0 Glycosyl Sulfoxides in Glycosylation Reactions .............................................. 367 Jing Zeng, Yan Liu, Wei Chen, Xiang Zhao, Lingkui Meng and Qian Wan: Top Curr Chem (Z) 2018, 376:27 (12, June 2018) https://doi.org/10.1007/s41061-018-0205-4 Chiral Sulfoxide Ligands in Asymmetric Catalysis ........................................ 399 Tao Jia, Min Wang and Jian Liao: Topics in Current Chemistry 2019, 377:8 (12, February 2019) https://doi.org/10.1007/s41061-019-0232-9 Sulfur‑Based Ylides in Transition‑Metal‑Catalysed Processes ..................... 429 James D. Neuhaus, Rik Oost, Jérémy Merad and Nuno Maulide: Top Curr Chem (Z) 2018, 376:15 (13, April 2018) https://doi.org/ 10.1007/s41061-018-0193-4 Preface Sulfur-containing molecule is a kind of sparkling structure in chemistry, which is widely applied in pharmaceuticals, agrochemicals, materials, and even flavors. The construction of diverse sulfur-containing molecules is of strategic importance in synthetic programs due to their widely applications. Furthermore, sulfur shows divergent functions and potencies in different oxidative states, which has led to rich chemistry of sulfur in organic synthesis. This collection introduces sulfur chemistry in organic synthesis and the appli- cation of sulfides. Thirteen contributions are organized in this collection. Prof. Jon T. Njardarson described the analysis of 254 sulfur-containing FDA-approved drugs, which offers a unique and comprehensive overview of the structural features of sulfur-containing drugs to date. Prof. Guang-Fu Yang and co-workers discussed sulfur-containing agrochemicals, contributing a state-of-art overview of selected leading sulfur-containing pesticidal chemical families. Prof. Turan Ozturk described thiophene-based organic semiconductors, classified in terms of their chemical structures and structure–property relationships. This chapter addresses sulfides as organic photovoltaics (OPVs), organic field-effect transistors (OFETs) and organic light emitting diodes (OLEDs). Prof. Justin Chalker displayed the synthesis of polymers via inverse vulcanization and their diverse applications. An outlook is presented to show future opportunities and challenges for further advancement of polymers made by inverse vulcanization. Prof. Chin-Fa Lee summarized the recent developments in the area of C–S coupling reaction through metal catalysis and other alternative processes. Prof. Hideki Yorimitsu described C–S bond activation by transition metal complexes and accordingly catalytically synthetic reactions involving C–S bond activation in due course. Prof. Toshiaki Murai presented an overview of fundamental aspects of thiocarbonyl motifs, such as thioaldehydes and thioketones. Prof. Thomas J. J. Müller summarized ring-forming multicomponent reactions for synthesizing thiophenes and their derivatives. We focused on the methodologies reported recently for the synthesis of polysulfide-containing com- pounds, with particular emphasis on unsymmetrical disulfides. Prof. Richard Glass highlighted the exciting applications of current research involving sulfur vii viii Preface radicals in bonding theory, organic synthesis, polymer chemistry, materials science, and biochemistry. The contribution from Prof. Qian Wan covers the establishment and development of sulfoxides as glycosyl donors in glycosylation reactions, with focus on their applications and postulated mechanisms. Prof. Jian Liao discussed recently prevalent chiral sulfoxide ligands in asymmetric catalytic reactions. Prof. Nuno Maulide summarized the cutting-edge developments in transition metal-catalyzed sulfonium/sulfoxonium ylide reactions, as well as a historical pers- pective. This sulfur chemistry topical collection will be helpful and useful for the organic chemistry professionals, who wish to understand the mysteries of sulfur chemistry deeply and comprehensively at the forefront. The suitable groups can be scientist, researcher and graduate students in chemistry. Many thanks to prominent sulfur experts for their contributions to this book. I personally would like to thank the editorial staff of Topics in Current Chemistry for advising on sulfur chemistry collection, which will produce enormous function and far-reaching to influence to the community associating with sulfur. Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University Top Curr Chem (Z) (2018) 376:5 https://doi.org/10.1007/s41061-018-0184-5 REVIEW Analysis of US FDA‑Approved Drugs Containing Sulfur Atoms Kevin A. Scott1,2 · Jon T. Njardarson1 Received: 20 November 2017 / Accepted: 5 January 2018 / Published online: 22 January 2018 © Springer International Publishing AG, part of Springer Nature 2018 Abstract In this review, we discuss all sulfur-containing FDA-approved drugs and their structures. The second section of the review is dedicated to structural analy- sis and is divided into 14 subsections, each focusing on one type of sulfur-contain- ing moiety. A concise graphical representation of each class features drugs that are organized on the basis of structural similarity, evolutionary relevance, and medical indication. This review offers a unique and comprehensive overview of the struc- tural features of all sulfur-containing FDA-approved drugs to date. Keywords Sulfonamide · Thioether · Sulfoxide · Sulfone · Sulfate · Sulfur heterocycle Abbreviations 6-APA 6 -Aminopenicillanic acid ADP A denosine diphosphate cGMP C yclic guanosine monophosphate COX-2 Cyclooxygenase-2 GERD Gastroesophageal reflux disease GPCR G protein-coupled receptor HIV Human immunodeficiency virus mRNA Messenger RNA NSAID Nonsteroidal anti-inflammatory drugs SMN1 S urvival motor neuron 1 Chapter 1 was originally published as Scott, K. A. & Njardarson, J. T. Top Curr Chem (Z) (2018) 376: 5. https://doi.org/10.1007/s41061-018-0184-5. * Jon T. Njardarson [email protected] 1 Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721, USA 2 Department of Pharmacology and Toxicology, University of Arizona, Tucson, AZ 85721, USA Reprinted from the journal 1 1 3
The list of books you might like
