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Progress in Inorganic Chemistry Volume 59 Advisory Board Progress in Inorganic Chemistry Volume 59 Advisory Board JACQUELINE K. BARTON CALIFORNIA INSTITUTE OF TECHNOLOGY, PASADENA, CALIFORNIA SHUNICHI FUKUZUMI OSAKA UNIVERSITY, OSAKA, JAPAN CLARK R. LANDIS UNIVERSITY OF WISCONSIN, MADISON, WISCONSIN NATHAN S. LEWIS CALIFORNIA INSTITUTE OF TECHNOLOGY, PASADENA, CALIFORNIA STEPHEN J. LIPPARD MASSACHUSETTS INSTITUTE OF TECHNOLOGY, CAMBRIDGE, MASSACHUSETTS JEFFREY R. LONG UNIVERSITY OF CALIFORNIA, BERKELEY, CALIFORNIA THOMAS E. MALLOUK PENNSYLVANIA STATE UNIVERSITY, UNIVERSITY PARK, PENNSYLVANIA TOBIN J. MARKS NORTHWESTERN UNIVERSITY, EVANSTON, ILLINOIS JAMES M. MAYER YALE UNIVERSITY, NEW HAVEN, CONNECTICUT DAVID MILSTEIN WEIZMANN INSTITUTE OF SCIENCE, REHOVOT, ISRAEL WONWOO NAM EWHA WOMANS UNIVERSITY, SEOUL, KOREA VIVIAN W. W. YAM UNIVERSITY OF HONG KONG, HONG KONG PROGRESS IN INORGANIC CHEMISTRY Edited by Kenneth D. Karlin DEPARTMENT OF CHEMISTRY JOHNS HOPKINS UNIVERSITY BALTIMORE,MARYLAND VOLUME 59 Cover Design: Wiley Copyright 2014 by John Wiley & Sons, Inc. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750–8400, fax (978) 750–4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748–6011, fax (201) 748–6008, or online at http://www.wiley.com/go/ permission. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762–2974, outside the United States at (317) 572–3993 or fax (317) 572–4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data is available. Library of Congress Catalog Number: 59013035 ISBN: 978-1-118-87016-7 Printed in the United States of America. 10987654321 Contents Chapter 1 Iron Catalysis in Synthetic Chemistry . .................... 1 SUJOY RANA,ATANU MODAK,SOHAM MAITY, TUHIN PATRA, AND DEBABRATA MAITI Chapter 2 A New Paradigm for Photodynamic Therapy Drug Design: Multifunctional, Supramolecular DNA Photomodification Agents Featuring Ru(II)/Os(II) Light Absorbers Coupled to Pt(II) or Rh(III) Bioactive Sites .......................... 189 JESSICA D. KNOLL AND KAREN J.BREWER Chapter 3 Selective Binding of Zn2 Complexes to Non-Canonical Thymine or Uracil in DNA or RNA . .................... 245 KEVIN E. SITERS,STEPHANIE A. SANDER, AND JANET R. MORROW Chapter 4 Progress Toward the Electrocatalytic Production of Liquid Fuels from Carbon Dioxide . .......................... 299 JOEL ROSENTHAL Chapter 5 Monomeric Dinitrosyl Iron Complexes: Synthesis and Reactivity . ......................................... 339 CAMLY T. TRAN,KELSEY M. SKODJE, AND EUNSUK KIM Chapter 6 Interactions of Nitrosoalkanes/arenes, Nitrosamines, Nitrosothiols, and Alkyl Nitrites with Metals ............... 381 NAN XU AND GEORGE B. RICHTER-ADDO Chapter 7 Aminopyridine Iron and Manganese Complexes as Molecular Catalysts for Challenging Oxidative Transformations . .................................... 447 ZOEL CODOLA,JULIO LLORET-FILLOL, AND MIQUEL COSTAS Subject Index .................................................. 533 Cumulative Index . .............................................. 561 v Iron Catalysis in Synthetic Chemistry SUJOY RANA, ATANU MODAK, SOHAM MAITY, TUHIN PATRA, AND DEBABRATA MAITI Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, India CONTENTS I. INTRODUCTION II. ADDITION REACTIONS A. Cycloadditions 1. The [2 + 2] Cycloaddition 2. The [3 + 2] Cycloaddition 3. The [2 + 2 + 2] Cycloaddition 4. The [4 + 2] Cycloaddition B. Cyclopropanation C. Aziridination and Aziridine Ring-Opening Reactions D. Carbometalation of C-C Unsaturated Bond E. Michael Addition F. Barbier-Type Reaction G. Kharasch Reaction III. THE C-C BOND FORMATIONS VIA C-H FUNCTIONALIZATION A. The C-H Arylation 1. Direct Arylation With Organometallic Reagents 2. Direct Arylation With Aryl Halides B. The C-C Bond Formation Via Cross-Dehydrogenative Coupling 1. The CDC Between Two sp3 C-H Bonds 2. The CDC Between sp3 and sp2 C-H Bonds 3. The CDC Between sp3 and sp C-H Bonds C. The C-C Bond Formation via Cross-Decarboxylative Coupling D. The C-C Bond Formation via Alkene Insertion E. Oxidative Coupling of Two C-H Bonds IV. THE C-H BOND OXIDATION A. Hydroxylation Progress in Inorganic Chemistry, Volume 59, First Edition. Edited by Kenneth D. Karlin. 2014 John Wiley & Sons, Inc. Published 2014 by John Wiley & Sons, Inc. 1 2 SUJOY RANA ET AL. B. Epoxidation C. cis-Dihydroxylation V. CROSS-COUPLING REACTIONS A. Alkenyl Derivatives as Coupling Partners B. Aryl Derivatives as Coupling Partners C. Alkyl Derivatives as Coupling Partners 1. Low-Valent Iron Complex in Cross-Coupling Reactions D. Acyl Derivatives as Coupling Partners E. Iron-Catalyzed C-O, C-S, and C-N Cross-Coupling Reaction F. Iron-Catalyzed Mizoraki–Heck Reaction G. Iron-Catalyzed Negishi Coupling Reaction H. Suzuki–Miyaura Coupling Reaction I. Sonogashira Reaction J. Mechanism of Cross-Coupling Reactions K. Hydrocarboxylation L. Enyne Cross-Coupling Reaction VI. DIRECT C-N BOND FORMATION VIA C-H OXIDATION VII. IRON-CATALYZED AMINATION A. Allylic Aminations B. Intramolecular Allylic Amination VIII. SULFOXIDATIONS AND SYNTHESIS OF SULFOXIMINES, SULFIMIDES, AND SULFOXIMIDES A. Sulfoxidation B. Synthesis of Sulfoximines, Sulfimides, and Sulfoximides 1. Mechanism IX. REDUCTION REACTIONS A. Hydrosilylation of Alkenes B. Hydrosilylation of Aldehydes and Ketones C. Hydrogenation of C-C Unsaturated Bonds D. Hydrogenation of Ketones E. Hydrogenation of Imines F. Reduction of Nitroarene to Anilines G. Hydrogenation of Carbon Dioxide and Bicarbonate H. Amide Reduction I. Reductive Aminations X. TRIFLUOROMETHYLATION XI. CONCLUSION ACKNOWLEDGMENTS ABBREVIATIONS REFERENCES IRON CATALYSIS IN SYNTHETIC CHEMISTRY 3 I. INTRODUCTION During the last few decades, transition metal catalysts, especially those on precious metals [e.g., palladium (Pd), rhodium (Rh), iridium (Ir), and ruthe- nium (Ru)] have proven to be efficient for a large number of applications. The success of transition metal based organometallic catalysts lies in the easy modification of their environment by ligand exchange. A very large number of different types of ligands can coordinate to transition metal ions. Once the ligands are coordinated, the reactivity of the metals may change dramatically. However, the limited availability of these metals, in order of decreasing risk (depletion): Au > Ir, Rh, Ru > Pt, Re, Pd), as well as their high price (Fig. 1) and significant toxicity, makes it desirable to search for more economical and environmental friendly alternatives. A possible solution to this problem could be the increased use of catalysts based on first-row transition metals, especially iron (Fe) (1). In contrast to synthetic precious metal catalysts, iron takes part in various biological systems as an essential key element and electron-transfer reactions. Due to its abundance, inexpensiveness, and environmentally benign nature, use of iron has increased significantly in the last two decades for synthetic transformation both in asymmetric synthesis and reaction methodology. This development encouraged us to summarize the use of iron catalysis in organic synthesis, which includes cycloadditions, C-C, C-N bond formation, redox, and other reactions. This chapter has been divided into different sections based on the reaction type. Figure 1. Comparison of prices for different transition metals (Sigma Aldrich). 4 SUJOY RANA ET AL. II. ADDITION REACTIONS A. Cycloadditions 1. The [2 + 2] Cycloaddition In 2001, Itoh and co-workers (2) demonstrated the [2 + 2] cyclodimerization of trans-anethol catalyzed by alumina supported iron(III) perchlorate. A C2 symmet- ric cyclobutane derivative was obtained in excellent yield (92%) at room tempera- ture (rt), though longer reaction time was required. They applied the same catalytic system for the cycloaddition of styrenes and quinones. However, 2,3-dihydro- benzofuran derivatives
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