Organophosphorus chemistry. Volume 47

462 Pages·2018·35.933 MB·English

by  Allen, David W., Loakes, David, Tebby, John C

Organophosphorus Chemistry
Volume 47
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A Specialist Periodical Report
Organophosphorus Chemistry
Volume 47
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55- A Review of the Literature Published between
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13 January 2016 and January 2017
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81 Editors
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9/9 David W. Allen, Sheffield Hallam University, Sheffield, UK
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0 David Loakes, Laboratory of Molecular Biology, Cambridge, UK
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10. John C. Tebby, Staffordshire University, Stoke-on-Trent, UK
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g | Authors
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c. Piotr Bałczewski, Centre of Molecular and Macromolecular
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bs.r Studies, Ło´dz´, and Jan Długosz University in Cze˛stochowa,
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p Poland
http:// A. S. Balueva, A. E. Arbuzov Institute of Organic and Physical
n Chemistry, Kazan, Russian Federation
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18 Goutam Brahmachari, Visva-Bharati University, Santiniketan, India
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h 2 Agnieszka Bodzioch, Centre of Molecular and Macromolecular
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ar Studies, Ło´dz´, Poland
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9 Ma´rio J. F. Calvete, University of Coimbra, Portugal
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n Rui M. B. Carrilho, University of Coimbra, Portugal
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d Vadapalli Chandrasekhar, Indian Institute of Technology,
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blis Kanpur, India
Pu Giulia Fiorani, Ca’ Foscari University of Venice, Italy
A. A. Karasik, A. E. Arbuzov Institute of Organic and Physical
Chemistry, Kazan, Russian Federation
G. Keglevich, Budapest University of Technology and Economics,
Hungary
Ramesh Mamidala, National Institute of Science Education and
Research, Bhubaneshwar, India
E. I. Musina, A. E. Arbuzov Institute of Organic and Physical Chemistry,
Kazan, Russian Federation
R. Suriya Narayanan, Indian Institute of Technology, Kanpur, India
Romana Pajkert, Jacobs University, Bremen, Germany
Mariette M. Pereira, University of Coimbra, Portugal
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Alvise Perosa, Ca’ Foscari University of Venice, Italy
Gerd-Volker Ro¨schenthaler, Jacobs University, Bremen, Germany
Maurizio Selva, Ca’ Foscari University of Venice, Italy
Krishnan Venkatasubbaiah, National Institute of Science Education
and Research, Bhubaneshwar, India
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Print ISBN: 978-1-78801-167-9
PDF ISBN: 978-1-78801-305-5
1 EPUB ISBN: 978-1-78801-463-2
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P0 ISSN: 0306-0713
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5- DOI: 10.1039/9781788013055
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80 A catalogue record for this book is available from the British Library
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97 r The Royal Society of Chemistry 2018
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0. All rights reserved
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g | Apart from fair dealing for the purposes of research for non-commercial
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s.r Copyright, Designs and Patents Act 1988 and the Copyright and Related
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Preface
David Allen,a David Loakesb and John Tebbyc
DOI: 10.1039/9781788013055-FP007
07 This volume, No. 47 in the series, (first published in 1970 under the
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P editorship of Professor Stuart Trippett), covers the literature of
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55- organophosphorus chemistry published in the period from January
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13 2016 to January 2017, andcontinues ourefforts to providean up-to-date
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88 survey of progress in this topic which continues to generate a vast
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81 amountofresearch.WewelcometoourteamofauthorsProfessorAndrey
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9/9 Karasik, Dr Elvira Musina and Dr Anna Balueva, from the Russian
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0 Academy of Sciences, A. E. Arbuzov Institute of Organic and Physical
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10. Chemistry,Kazan,Russia,whohavetakenoverauthorshipofthechapter
oi: onthechemistryofphosphines,previouslycontributed(sincevolume8)
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g | by Professor David Allen, who continues as aco-editor ofthisseries. We
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c. again welcome to our team of authors Professor Goutam Brahmachari,
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s.r who has contributed a further guest chapter reviewing progress in
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p green and energy-efficient synthetic approaches in organophosphorus
http:// chemistry in 2016 and extending the coverage of this topic in recent
n volumes.
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8 The continuing vitality of research in phosphorus chemistry was
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2 demonstrated at the 21st International Conference on Phosphorus
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arc Chemistry,heldinKazan,RussiafromJune5–10,2016.Papersfromthe
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9 20th International Conference have now been published in a special
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n edition of Phosphorus, Sulfur and Silicon, 2016, 191, issue 11–12. Sadly,
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d we must note the passing in 2016 of two prominent members of the
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h
s organophosphoruscommunity,ProfessorJohnG.VerkadeandProfessor
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u Harry R. Hudson, both of whom made outstanding and very significant
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contributions to our area of research.
The annual survey of the literature relating to the chemistry of
traditionalphosphinescontainingonlyP–CandP–Hbondsincludesthe
synthesis of new phosphines classified according to the synthetic
approaches used, data concerning the reactivity of phosphines, (mainly
the attack of phosphorus at carbon or other atoms, excluding metal
complexation, and the formation of P(V) derivatives of phosphines) and
the application of phosphines in organocatalysis and other fields of
chemistry or adjacent sciences.
The chapter relating to tervalent phosphorus acid derivatives includes
syntheticmethodologiestohalogenophosphoruscompounds,phosphorus
amides (aminophosphines, phosphoramidites and diamidophosphites),
aBiomedicalResearchCentre,SheffieldHallamUniversity,SheffieldUKS11WB,UK
bMedicalResearchCouncil,LaboratoryofMolecularBiology,HillsRoad,
CambridgeUKCB20QH,UK
cDivisionofChemistry,FacultyofSciences,StaffordshireUniversity,Stoke-on-Trent
UKST42DE,UK
OrganophosphorusChem.,2018,47,vii–ix | vii
(cid:2)c TheRoyalSocietyofChemistry2018
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phosphorus esters (phosphinites, phosphonites and phosphites) and
mixedphosphoruscompoundsbearingtwodifferenttervalentphosphorus
moieties. A critical selectionof their applications is briefly assessed, with
anemphasisonthecatalyticapplicationsofligandsandmetalcomplexes.
In phosphine chalcogenide chemistry, interest in the development of
methodsfortheirsynthesis,andtheirapplicationsasnewcomponentsin
opto-electronic devices, has again shown considerable growth. Their
7 additions to unsaturated substrates and P–C coupling reactions, repre-
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P0 sent a very active area. The chemistry of phosphonium salts and related
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5- ylides also continues to show remarkable activity, with particular refer-
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30 ence to catalytic applications and, in particular, to the synthesis and
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80 applications of phosphonium salts as ionic liquids that display higher
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17 thermaland electrochemical stabilities comparedto relatedammonium
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97 salts and which also have potential as new solvents in organic synthesis
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3 and as stabilisers for nanoparticle systems.
0
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0. Unfortunately, the usual chapter on nucleic acids and mono-
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oi: nucleotides is missing from this volume as a result of professional
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g | difficulties experienced by the authors. However, they hope to provide a
c.or two-year survey covering 2016 and 2017 in the next volume. In addition,
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s.r it has been some time since we have included a chapter on oligonu-
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u cleotides, and we would welcome approaches from prospective authors
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p:// who might consider taking on this chapter in future volumes.
n htt The quinquevalent organophosphorus acids chapter describes com-
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8 poundspossessing,inadditiontothephosphorylgroupP¼O,threeP–O
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20 bonds (phosphates), two P–O bonds and one P–C bond (phosphonates)
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c and one P–O and two P–C bonds (phosphinates), and has been divided
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M to cover synthesis, reactions and biological aspects. Each section covers
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2 a variety of topics, such as new reagents, new methods of synthesis,
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d o total and stereocontrolled syntheses, multicomponent reactions as well
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h as biological investigations. Reintroduced into this chapter is a section
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ubli on the synthesis and applications of phosphoric acids as catalysts. The
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area of phosphoric acids and in particular phosphinic acids and their
derivatives has shown particular growth during this review period.
Interest in methods for the synthesis of penta- and hexa-coordinated
compounds has continued. The section on pentacoordinated com-
pounds has short reviews on the chemistry of chiral, cyclic and bicyclic
pentacoordinated phosphoranes, and well-established routes to caged
phosphoranes have also been presented. The utility of dichlorotri-
phenylphosphorane, generated in situ as an excellent chlorinating
agent for carboxylic acids, has been demonstrated, whereas a novel
pentacoordinated compound bearing a P-P bond has been isolated and
characterized. Fluoride ion affinity studies of selected perfluorophos-
phoranes showed that they are powerful Lewis acids. Hypervalent
states can be a driving force in metal catalysis, transition-metal-free
arylation of carbonyl derivatives and in explaining the mechanism of
substitution of chiral phosphoryl chlorides with organometallic reagents.
Five-coordinated phosphoranes exhibit catalytic activity in polymer-
ization and in the preparation of new complex ylides. Pentacoordinated
phosphorus transition states are involved in the construction of cyclic
viii | OrganophosphorusChem.,2018,47,vii–ix
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aryl phosphoimidazoles. The hydrolytic cleavage of a phosphate ester
catalysed by copper complexes may involve hypervalent phosphorus(V)
intermediates and hexacoordinated compounds have been cited in the
synthesis, properties and various applications of phosphorus(V) com-
plexes of porphyrins.
Various types of phosphazenes have been investigated. The interest
stems from various aspects including structure, bonding, reactivity and
7 applications.Cyclophosphazenescontinuetobestudiedwithgreatvigour.
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5- substituents to produce alkyl-/arylamino-, alkoxy-, aryloxy-, alkyl-, aryl-,
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30 and halogeno/pseudohalogeno-products. The close inter-relationship
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80 betweencyclicandpolymericderivativesisofconsiderableinterestinthis
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17 field. As in previous years there has been keen interest in acyclic phos-
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97 phazenesfromseveralpointsofviewincludingtheirpotentialasligands
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3 for binding main-group, transition metal and lanthanide ions as well
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0. as aspects related to their basicity. The subject matter in this chapter
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oi: is discussed according to the following sub-sections: (a) acyclic phos-
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g | phazenes or iminophosphoranes, (b) cyclophosphazenes, (c) polyphos-
c.or phazenesandrelatedpolymers,(d)hybridsystemsand(e)applications.
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OrganophosphorusChem.,2018,47,vii–ix | ix
Author Biographies
DOI: 10.1039/9781788013055-FP010
Piotr Bałczewski studied chemistry at the
0 Technical University of Łod´z. MSc/PhD
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P theses(P/S/Siandcyclopentanoidchemistry)
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5- werewithProf.M.MikołajczykattheCentre
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3 of Molecular and Macromolecular Studies
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8 (CM&MS),PolishAcademyofSciences(PAS),
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1 Ło´d´z. Doctoral studies at the Institute of
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9 Organic Chemistry, PAS, Warsaw then a
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03 postdoctoralperiodatManchesterUniversity
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0. (UK) in alkaloid chemistry (Prof. J. A. Joule)
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oi: led to habilitation and appointment as full
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g | professoratCM&MS PAS,Ło´d´z.Hecurrently
c.or leads materials research groups at CM&MS
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s.r PAS,Łod´zandtheJanDługoszUniversityinCz˛estochowa,andiscurrently
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pu Vice-President of the Polish Chemical Society.
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8 Dr Anna S. Balueva graduated from Kazan
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2 StateUniversityin1984.Sincethattimeshehas
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arc occupied research positions in A. E. Arbuzov
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Institute of Organic and Physical Chemistry
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n 2 KSC RAS (IOPC), Kazan. Since 2000 she has
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d been a senior researcher of the laboratory of
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sh organometallic and coordination compounds
ubli ofIOPC.ShereceivedherPhDdegreein1988
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under the supervision of DrSci O. A. Erastov.
Her research interests includes the synthetic
and coordination chemistry of functionalized
tertiary phosphines (in particular P,N-
containinghetero-andmacrocycles).
x | OrganophosphorusChem.,2018,47,x–xviii
(cid:2)c TheRoyalSocietyofChemistry2018