Alkane Functionalization

Presents state-of-the-art information concerning the syntheses of valuable functionalized organic compounds from alkanes, with a focus on simple, mild, and green catalytic processes 

Alkane Functionalization offers a comprehensive review of the state-of-the-art of catalytic functionalization of alkanes under mild and green conditions. Written by a team of leading experts on the topic, the book examines the latest research developments in the synthesis of valuable functionalized organic compounds from alkanes.

The authors describe the various modes of interaction of alkanes with metal centres and examine theoxidative alkane functionalization upon C-O bond formation. They address the many types of mechanisms, discuss typical catalytic systems and highlight the strategies inspired by biological catalytic systems. The book also describes alkane functionalization upon C-heteroatom bond formation as well as oxidative and non-oxidative approaches. In addition, the book explores non-transition metal catalysts and metal-free catalytic systems and presents selected types of functionalization of sp3 C-H bonds pertaining to substrates other than alkanes. This important resource:

• Presents a guide to the most recent advances concerning the syntheses of valuable functionalized organic compounds from alkanes
• Contains information from leading experts on the topic
• Offers information on the catalytic functionalization of alkanes that allows for improved simplicity and sustainability compared to current multi-stage industrial processes
• Explores the challenges inherent with the application of alkanes as starting materials for syntheses of added value functionalized organic compounds

ARMANDO J. L. POMBEIRO is full professor at the Instituto Superior Técnico (IST) of the Universidade de Lisboa (ULisboa), Portugal. He is President of the College of Chemistry of ULisboa and of the Centro de Química Estrutural (IST), Director of the Catalysis and Sustainability (CATSUS) PhD program, and full member of the Academy of Sciences of Lisbon. His research addresses activation of small molecules with industrial, environmental or biological significance, including metal-mediated synthesis and catalysis (e.g., functionalization of alkanes), self-assembly of polynuclear and supramolecular structures, non-covalent interactions in synthesis, crystal engineering of coordination compounds, molecular electrochemistry and theoretical studies. He authored or edited 7 books, (co-)authored over 800 research publications and 40 patents. His work has received over 20,000 citations and he has an h index of over 60 (Web of Science). He is the recipient of several scientific prizes, including from the Chemical Societies of France, Royal Spanish and Portugal, as well as from the Technical University of Lisbon, and the Vanadis Award.

M. FÁTIMA C. GUEDES DA SILVA is an Associate Professor at Instituto Superior Técnico, Lisbon, Portugal. She is the Coordinator of the research group of Coordination Chemistry and Catalysis of the Centro de Química Estrutural, member of the Coordination Commission of this Centre and of the Directive Board of the Catalysis and Sustainability (CATSUS) PhD program. Her main research interests include: structural determination, by X-ray diffraction analysis, of metal complexes and organic compounds, metal polynuclear assemblies and supramolecular structures; activation, by transition metal centres, of small molecules with biological, pharmacological, environmental or industrial significance; metal mediated synthesis and catalysis; molecular electrochemistry and electrocatalysis; mechanistic investigation of fast reactions mainly by digital simulation of cyclic voltammetry. She co-authored ca. 300 research publications, 13 patents. She was awarded the Scientific Prize Universidade de Lisboa / CGD and the Scientific Prize of the Portuguese Electrochemical Society.

About the editors

List of contributors

Preface
Armando J.L. Pombeiro and M. Fátima C. Guedes da Silva

Chapter 1 Alkane Functionalization: Introduction And Overview
Armando J.L. Pombeiro

PART I -  C-O BOND FORMATION. HYDROXYLATION AND OTHER OXYGENATION REACTIONS

Chapter 2 Activation and oxidative functionalization of alkanes with noble-metal catalysts: Molecular mechanisms
Evgeniy G. Chepaikin

Chapter 3 Alkane-oxidizing systems based on metal complexes. Radical versus non-radical mechanisms
Georgiy B. Shul’pin

Chapter 4 Reactions of alkyl radicals in aqueous solutions
Dan meyerstein

Chapter 5 C–H bond oxidation with transition metal based carbene complexes
Bruno Dominelli, Anja C. Lindhorst,Fritz E. Kühn

Chapter 6 Alkane oxidation with C-scorpionate metal complexes
Luísa M. D. R. S. Martins

Chapter 7 Alkane oxidation with multinuclear heterometallic catalysts
Dmytro S. Nesterov, Oksana V. Nesterova and Armando J.L. Pombeiro

Chapter 8 Oxidative functionalization of methane on heterogeneous catalysts
Maricruz Sanchez-Sanchez and Johannes A. Lercher

Chapter 9 Gas-phase oxidation of alkanes
Fabrizio Cavani, Alessandro Chieregato, Jose Manuel Lopez Nieto,Jean-Marc M. Millet

PART II - BIOINSPIRED ALKANE FUNCTIONALIZATION

Chapter 10 Recent developments of bio-inspired approaches to functionalization of light alkanes
Alexander B. Sorokin

Chapter 11 Regioselectivity of non-heme iron catalysts for C-H activation
Christian R. Goldsmith

Chapter 12 Imine-based Iron and Manganese Complexes as Catalysts for Alkane Functionalization
Giorgio Olivo, Osvaldo Lanzalunga,Stefano Di Stefano

Chapter 13 Alkane oxidation with biologically inspired nonheme iron catalysts based in the triazacyclononane ligand scaffold 
Miquel Costas

Chapter 14 The nature of high-valent oxometal intermediates of iron-aminopyridine mediated oxidations
Oleg Y. Lyakin, konstantin P. Bryliakov, Evgenii P. Talsi

Chapter 15 Selective Oxidation of Alkanes by Metallo-Monooxygenases and their Nano-Biomimetics
Chih-Cheng Liu,Yi-FangTtsai,Wondemagegn H. Wanna,Ravirala Ramu, Damodar Janmanchi, Sunney I. Chan,Steve S.-F. Yu

Chapter 16 Alkane oxidation with vanadium and copper catalysts
Manas Sutradhar, Luísa M.D.R.S. Martins, M. Fátima C. Guedes da Silva, ArmandoJ. L. Pombeiro

PART III – C-B, C-C AND C-N BOND FORMATION

Chapter 17 Catalytic borylation of methane: combining computational and high-throughput screening approaches to discover a new catalyst
Pavel Zatsepin, Dieter Sorsche, Seihwan Ahn,Mu-Hyun Baik, Daniel J. Mindiola

Chapter 18 Alkane carbonylation and carbene insertion reactions
Ana M. Faisca Phillips and Armando J. L. Pombeiro

Chapter 19 Catalytic alkane amidation and related reactions
Dmytro S. Nesterov, Luís M. T. Frija, Armando J. L. Pombeiro, Maximilian N. Kopylovich

PART IV – DEHYDROGENATION REACTIONS

Chapter 20 Oxidative and non-oxidative routes to alkane dehydrogenation
Jay A. Labinger

Chapter 21 Dehydrogenation of alkanes using molecular catalysts
Huaquan Fang, Guixia Liu, Zheng Huang

PART V – UNCONVENTIONAL SYSTEMS

Chapter 22 Non-transition metal catalyzed oxidation of alkanes with peroxides
Maxim L. Kuznetsov

Chapter 23 Metal-free functionalization of alkanes
Jincan Zhao,Jianlin Han

Chapter 24 Alkane functionalization under unconventional conditions: in ionic liquid, in supercritical co₂ and microwave assisted
Ana P.C. Ribeiro,Eelisabete C.B.A. Alegria, António Palavra,Aarmando J.L. Pombeiro

Chapter 25 Noncovalent interactions in alkane chemistry
Kamran T. Mahmudov,M. Fátima C. Guedes da Silva, Fedor I. Zubkov, Armando J. L. Pombeiro

Chapter 26 Alkane complexation
Robert H. Crabtree

Chapter 27 Alkane related C-H bond activation and functionalization of aliphatic amines
Christian Bruneau, Mathieu Achard

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