Frontiers of Green Catalytic Selective Oxidations

298 Pages·2019·21.414 MB·English

by  Konstantin P. Bryliakov

Green Chemistry and Sustainable Technology
Konstantin P. Bryliakov Editor
Frontiers of Green
Catalytic Selective
Oxidations
Green Chemistry and Sustainable Technology
Series Editors
Liang-Nian He
State Key Lab of Elemento-Organic Chemistry, Nankai University, Tianjin, China
Robin D. Rogers
Department of Chemistry, The University of Alabama, Tuscaloosa, USA
Dangsheng Su
DalianInstituteofChemicalPhysics,ChineseAcademyofSciences,Dalian,China
Pietro Tundo
Department of Environmental Sciences, Informatics and Statistics, Ca’ Foscari
University of Venice, Venice, Italy
Z. Conrad Zhang
DalianInstituteofChemicalPhysics,ChineseAcademyofSciences,Dalian,China
Aims and Scope
The series Green Chemistry and Sustainable Technology aims to present
cutting-edge research and important advances in green chemistry, green chemical
engineering and sustainable industrial technology. The scope of coverage includes
(but is not limited to):
– Environmentally benign chemical synthesis and processes (green catalysis,
green solvents and reagents, atom-economy synthetic methods etc.)
– Green chemicals and energy produced from renewable resources (biomass,
carbon dioxide etc.)
– Novel materials and technologies for energy production and storage (bio-fuels
and bioenergies, hydrogen, fuel cells, solar cells, lithium-ion batteries etc.)
– Green chemical engineering processes (process integration, materials diversity,
energy saving, waste minimization, efficient separation processes etc.)
– Green technologies for environmental sustainability (carbon dioxide capture,
waste and harmful chemicals treatment, pollution prevention, environmental
redemption etc.)
The series Green Chemistry and Sustainable Technology is intended to provide an
accessible reference resource for postgraduate students, academic researchers and
industrial professionals who are interested in green chemistry and technologies for
sustainable development.
More information about this series at http://www.springer.com/series/11661
Konstantin P. Bryliakov
Editor
Frontiers of Green Catalytic
Selective Oxidations
123
Editor
Konstantin P. Bryliakov
Russian Academy of Sciences
Boreskov Institute of Catalysis
Novosibirsk, Russia
ISSN 2196-6982 ISSN 2196-6990 (electronic)
Green Chemistry andSustainable Technology
ISBN978-981-32-9750-0 ISBN978-981-32-9751-7 (eBook)
https://doi.org/10.1007/978-981-32-9751-7
©SpringerNatureSingaporePteLtd.2019
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Preface
Catalyzed processes of selective oxidation of hydrocarbons, as well as of complex
organic substrates, have had a long and illustrious track record, nowadays consti-
tuting one of the foundation stones of modern synthetic chemistry. Nevertheless,
new developments in the field, mostly focused on enhancing the oxidation selec-
tivity and improving their environmental sustainability, but also launching previ-
ously unachieved catalytic reactivity, have continued apace to this day, thus
suggesting that the field is far from its maturity.
This book embodies contributions of recognized experts who have surveyed
recent developments at the forefront of the environmentally sustainable catalytic
oxidations,rangingfromthewell-establishedchemo-andstereoselectiveoxidations
ofolefins,sulfides,alcohols,aswellasthemuchlessdevelopedC–Hoxidationsof
aromatic and aliphatic substrates, including methane. In all cases, most catalyst
systems relying on the environmentally benign oxidants H O and O are dis-
2 2 2
cussed.“Green”aspectsofthoseoxidations,suchastheprocessatomeconomy,the
nature of reaction solvents, are considered.
We hope that this collection can serve as a reference book for professionals, as
wellasaguideandinspirationforstudentsandyoungresearchers atthebeginning
of their career. The topics of the chapters have been selected in a more or less
voluntaristic fashion, in agreement with our current vision of the most challenging
research directions in the field, holding the promise of significantly enriching,
perhaps even revolutionizing the chemical industry in a one-generation time hori-
zon. At the same time, we would like to stress that current selective oxidation
catalysisisnotlimitedtothetopicsconsideredhereandprovidesenoughalternative
opportunities for investing research efforts that can appear highly rewarding.
Novosibirsk, Russia Konstantin P. Bryliakov
v
Contents
1 Metal-Catalyzed Oxidation of C–H Compounds with Peroxides
in Unconventional Solvents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
Georgiy B. Shul’pin
2 Low-Temperature Catalytic Selective Oxidation of Methane
to Methanol. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
Nishtha Agarwal, Stuart H. Taylor and Graham J. Hutchings
3 Recent Progress in Selective Oxidations with Hydrogen Peroxide
Catalyzed by Polyoxometalates . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61
Oxana A. Kholdeeva
4 Recent Developments in the Catalytic Asymmetric Sulfoxidation
Reactions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93
Konstantin Volcho
5 Non-covalent Organocatalytic Approach in the Asymmetric
Epoxidation of Electron-Poor Alkenes: Recent Developments. . . . . 113
Alessandra Lattanzi
6 Green Oxidative Kinetic Resolutions of Secondary Alcohols. . . . . . 137
Hélène Pellissier
7 Asymmetric Epoxidation Catalyzed by Biologically Inspired
Non-heme Iron Catalysts and Hydrogen Peroxide . . . . . . . . . . . . . 161
Laia Vicens and Miquel Costas
8 Recent Advances in Bioinspired Asymmetric Epoxidations
with Hydrogen Peroxide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 199
Roman V. Ottenbacher
9 Organometallic C–H Oxidation with O Mediated by Soluble
2
Group 10 Metal Complexes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 223
Andrei N. Vedernikov
vii
viii Contents
10 Direct C–H Oxidation of Aromatic Substrates in the Presence
of Biomimetic Iron Complexes . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253
Oleg Y. Lyakin and Evgenii P. Talsi
11 Catalytic Asymmetric C–H Oxidation with H O and O . . . . . . . . 277
2 2 2
Konstantin P. Bryliakov
Contributors
Nishtha Agarwal Cardiff Catalysis Institute, Cardiff, UK
Konstantin P. Bryliakov Novosibirsk State University, Novosibirsk, Russian
Federation;
Boreskov Institute of Catalysis, Novosibirsk, Russian Federation
Miquel Costas Departament de Química i Institut de Química Computacional i
Catàlisi, Facultat de Ciències, Girona, Catalonia, Spain
Graham J. Hutchings Cardiff Catalysis Institute, Cardiff, UK
Oxana A. Kholdeeva Boreskov Institute of Catalysis, Siberian Branch of the
Russian Academy of Sciences, Novosibirsk, Russia;
Novosibirsk State University, Novosibirsk, Russia
Alessandra Lattanzi Dipartimento di Chimica e Biologia, Università di Salerno,
Fisciano, Italy
Oleg Y. Lyakin Boreskov Institute of Catalysis, Novosibirsk, Russia;
Novosibirsk State University, Novosibirsk, Russia
Roman V. Ottenbacher Novosibirsk State University, Novosibirsk, Russia;
Boreskov Institute of Catalysis, Novosibirsk, Russia
Hélène Pellissier Aix-Marseille Université, CNRS, Marseille, France
Georgiy B. Shul’pin Department of Dynamics of Chemical and Biological
Processes, Semenov Institute of Chemical Physics, Russian Academy of Sciences,
Ulitsa Kosygina, Moscow, Russia;
People’s Friendship University of Russia, Moscow, Russia
Evgenii P. Talsi Boreskov Institute of Catalysis, Novosibirsk, Russia;
Novosibirsk State University, Novosibirsk, Russia
Stuart H. Taylor Cardiff Catalysis Institute, Cardiff, UK
ix
x Contributors
AndreiN.Vedernikov DepartmentofChemistryandBiochemistry,Universityof
Maryland, College Park, MD, USA
Laia Vicens Departament de Química i Institut de Química Computacional i
Catàlisi, Facultat de Ciències, Girona, Catalonia, Spain
Konstantin Volcho Novosibirsk Institute of Organic Chemistry, Novosibirsk,
Russia