Organophosphorus chemistry. Volume 49

410 Pages·2020·42.598 MB·English

by  Allen, David W., Higham, Lee J., Loakes, David, Tebby, John C

Organophosphorus Chemistry
Volume 49
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A Specialist Periodical Report
Organophosphorus Chemistry
Volume 49
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91- Editors
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19 David W. Allen, Sheffield Hallam University, Sheffield, UK
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88 David Loakes, Laboratory of Molecular Biology, Cambridge, UK
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81 Lee J. Higham, Newcastle University, UK
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9/9 John C. Tebby, Staffordshire University, Stoke-on-Trent, UK
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10. Authors
oi: PiotrBałczewski,PolishAcademyofSciencesandJanDługoszUniversity
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g | in Cze˛stochowa, Poland
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c. A. S. Balueva, A. E. Arbuzov Institute of Organic and Physical Chemistry
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s.r KSC RAS, Russian Federation
b
u
p Goutam Brahmachari, Visva-Bharati University, India
ps:// Ma´rio J. F. Calvete, University of Coimbra, Portugal
n htt Rui M. B. Carrilho, University of Coimbra, Portugal
o
0 Amit Chakraborty, Indian Institute of Technology Kanpur, India
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20 Vadapalli Chandrasekhar, Tata Institute of Fundamental Research
pril Hyderabad and Indian Institute of Technology Kanpur, India
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4 Giulia Fiorani, Ca’ Foscari University of Venice, Italy
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on A.A.Karasik,A.E.ArbuzovInstituteofOrganicandPhysicalChemistryKSC
d RAS, Russian Federation
e
h
blis G.Keglevich,BudapestUniversityofTechnologyandEconomics,Hungary
Pu E.I.Musina,A.E.ArbuzovInstituteofOrganicandPhysicalChemistryKSC
RAS, Russian Federation
Romana Pajkert, Jacobs University, Germany
Mariette M. Pereira, University of Coimbra, Portugal
Alvise Perosa, Ca’ Foscari University of Venice, Italy
Sara M. A. Pinto, University of Coimbra, Portugal
Gerd-Volker Ro¨schenthaler, Jacobs University, Germany
A.V.Shamsieva,A.E.Arbuzov,InstituteofOrganicandPhysicalChemistry
KSC RAS, Russian Federation
Maurizio Selva, Ca’ Foscari University of Venice, Italy
Joanna Wilk, Polish Academy of Sciences, Poland
View Online
Print ISBN: 978-1-78801-864-7
PDF ISBN: 978-1-78801-949-1
EPUB ISBN: 978-1-78801-950-7
1 Print ISSN: 0306-0713
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P0 Electronic ISSN: 1465-1904
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1- DOI: 10.1039/9781788019491
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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 2020
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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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Preface
David Allen,aDavid Loakes,bLee Highamcand John Tebbyd
DOI: 10.1039/9781788019491-FP005
5 This volume, No. 49 in the series, (first published in 1970 under the
0
0
P editorship of Professor Stuart Trippett), covers the literature of organo-
F
91- phosphorus chemistry published in the period from January 2018 to
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19 January2019,andcontinuesoureffortstoprovideanup-to-datesurveyof
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88 progress in this topic, which continues to generate a vast amount of
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81 research. We continue to be fortunate in securing contributions from a
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9 team of international authors from Germany, Poland, Portugal, Italy,
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03 Russia,HungaryandIndia.Thisyear,wewelcometoourteamofEditors,
1
0. Dr Lee Higham,of the School ofNatural andEnvironmental Sciences in
1
oi: theUniversityofNewcastle,whowilltakeoverthedirectionandplanning
d
g | of this series from volume 50. The continuing vitality of research in
or
c. phosphorus chemistry was demonstrated at the 22nd International
s
s.r Conference on Phosphorus Chemistry, held in Budapest in July 2018.
b
u
p Papers from this conference have been published in Phosphorus, Sulfur,
ps:// Silicon and Related Elements, 2019, volume 194, pp. 269–613.
htt The annual survey of the literature relating to the chemistry of tradi-
n
0 o tional phosphines containing only P–C and P–H bonds again includes
2
0 the synthesis of new phosphines, classified according to the synthetic
2
pril approaches used, data concerning the reactivity of phosphines, (mainly
A
4 the attack of phosphorus at carbon or other atoms, excluding metal
1
on complexation, and the formation of P(V) derivatives of phosphines) and
d the application of phosphines in organocatalysis and other fields of
e
h
blis chemistry or adjacent sciences.
u The chapter relating to tervalent phosphorus acid derivatives includes
P
syntheticmethodologiestohalogenophosphoruscompounds,phosphorus
amides (aminophosphines, phosphoramidites and diamidophosphites),
phosphorus esters (phosphinites, phosphonites and phosphites) and
mixedphosphoruscompoundsbearingtwodifferenttervalentphosphorus
moieties. A critical selection of their applications is briefly assessed, with
an emphasis on the catalytic applications of ligands and their metal
complexes.
In phosphine chalcogenide chemistry, the development of methods
for their synthesis, and their applications as new components in opto-
electronic devices, has again shown considerable growth. Their additions
aBiomedicalResearchCentre,SheffieldHallamUniversity,SheffieldS11WB,UK
bMedicalResearchCouncil,LaboratoryofMolecularBiology,HillsRoad,
CambridgeCB20QH,UK
cSchoolofNaturalandEnvironmentalSciences,NewcastleUniversity,Newcastle
uponTyneNE17RU,UK
dDivisionofChemistry,FacultyofSciences,StaffordshireUniversity,Stoke-on-Trent
ST42DE,UK
OrganophosphorusChem.,2020,49,v–vii | v
(cid:2)c TheRoyalSocietyofChemistry2020
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tounsaturatedsubstratesandP–Ccouplingreactions,continuetopresent
a very active area.
Thechemistryofphosphoniumsaltsandrelatedylidesalsocontinues
to show remarkable vitality, with particular reference to catalytic appli-
cations and, in particular, to the synthesis and applications of phos-
phonium salts as ionic liquids that display higher thermal and
electrochemical stabilities compared to related ammonium salts and
5 which also have potential as new solvents in organic synthesis and as
0
P0 stabilisers for nanoparticle systems.
F
1- In this volume, we regret that we are unable to provide a report of
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94 progressinthechemistryofnucleicacidsandmononucleotides.Norhas
1
80 it been possible to find authors willing to cover progress in the related
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17 areas of oligo-, and poly-nucleotides. However, the quinquevalent
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97 organophosphorus acids area continues to grow in importance and
9/
3 activity. This chapter again reports progress in the chemistry of com-
0
0.1 poundspossessing,inadditiontothephosphorylgroupPQO,threeP–O
1
oi: bonds (phosphates), two P–O bonds and one P–C bond (phosphonates)
d
g | and one P–O and two P–C bonds (phosphinates), and is structured to
or cover synthesis, reactions and biological aspects. Each section covers a
c.
s.rs variety of topics, such as new reagents, new methods of synthesis, total
b
u and stereocontrolled syntheses, multicomponent reactions as well as
p
s:// biological investigations. The area of phosphoric acids and their deriva-
p
htt tives has again shown particular growth during this review period. The
n
o interest in phosphoric, phosphinic and phosphonic acids as catalysts
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02 grows constantly year-on-year, and chiral phosphorus(V) acids have been
2
pril used in a vast array of chemical reactions.
A Work on five- and six-coordinate phosphorus compounds and their
4
1 derivativesremainsasignificantareaofinterest,althoughthechemistry
d on of five-coordinate systems continues to dominate. This year’s review is
e
h divided into the above main subsections i.e. five coordinate- and six
s
ubli coordinate-compounds. The former includes studies of synthesis, struc-
P
ture and reactivity as well as their involvement as intermediates and
transition states. In this respect, a synthetic strategy for novel metallo-
phosphoranes,togetherwiththechemistryofselectedspirophosphoranes
and fluorinated phosphoranes, have been described. Moreover, fragmen-
tation pathways of aryloxyspirophosphoranes have also been proposed.
Theinvolvementofpentacoordinatedintermediatesortransitionstatesin
phosphine-mediated phosphodiester cleavage reactions have been
reviewed. The importance of pentacoordinated species as key intermedi-
ates in the oligomerization of isocyanates, monosaccharides and the
polymerisation of cyclic ethylene phosphate, has been confirmed. With
respect to hexacoordinated compounds, there has been limited attention
paidtothesynthesisandapplicationofnovelanions.However,areporton
the preparation of a neutral hexacoordinate phosphorus-ruthenium com-
plex has appeared.
The phosphazene chapter covers acyclic phosphazenes, cyclophos-
phazenes and polyphosphazenes. Among the many examples presented,
notable personal highlights with potential biological applications
include the utilisation of the PQN bond for bioconjugation via the
vi | OrganophosphorusChem.,2020,49,v–vii
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Staudinger reaction of an activated 2,6-dichlorophenylazide motif,
to allow for chemical modification of proteins in live cells, whilst
tris(o-phenylenedioxy)cyclotriphosphazene has shown an ability to trap
radicals such as phenylnitrosylnitroxide, which may be exploited to
provide clarification of chemical or biological structures of nanomater-
ials, whilst nanovesicles based on amphiphilic polyphosphazenes have
been shown to improve drug delivery of anti-cancer drugs. Elsewhere,
5 excitingdevelopmentsinphosphazene-actinidechemistryhaveemerged:
0
P0 exotic examples of U(IV) complexes containing a well-defined UQC bond
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1- have been prepared, which appear to demonstrate 3-centre P–C–U
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94 p-bonding, and covalent organic framework type networks prepared
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880 from N3P3Cl6 and phloroglucinol were shown to selectively separate
817 (UO2)21 from other metal ions. The same phosphorus precursor reacted
97 with barbituric acid to give covalent organic networks capable of redu-
9/
3 cing carbon dioxide to methane under photocatalytic conditions. Chiral
0
1
0. phosphazenes based on biaryl and P-spiro backboneswerealso reported
1
oi: tobeeffectiveinanumberofcatalyticenantioselectivetransformations.
d
g | Finally, we have another guest chapter from Professor Goutam
or Brahmachari, reviewing progress in green and energy-efficient synthetic
c.
s.rs approaches in organophosphorus chemistry in 2018, and extending the
b
u coverage of this topic in recent volumes.
p
s://
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htt D. W. Allen
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o D. Loakes
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02 L. J. Higham
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pril J. C. Tebby
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OrganophosphorusChem.,2020,49,v–vii | vii
Author Biographies
DOI: 10.1039/9781788019491-FP008
Piotr Bałczewski studied chemistry at the
8 Technical University of Łod´z. MSc/PhD
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P0 theses(P/S/Siandcyclopentanoidchemistry)
F
1- werewithProf.M.MikołajczykattheCentre
9
4
9 of Molecular and Macromolecular Studies
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8 (CM&MS),PolishAcademyofSciences(PAS),
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17 Ło´d´z. Doctoral studies at the Institute of
8
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9 Organic Chemistry, PAS, Warsaw then a
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3 postdoctoral period at Manchester Uni-
0
1
0. versity (UK) inalkaloidchemistry (Prof. J. A.
1
oi: Joule) led to habilitation and appointment
d
g | as full professor at CM&MS PAS, Ło´d´z and
c.or the Jan Długosz University in Cz˛estochowa.
s
s.r Hecurrentlyleadsmaterialsresearchgroupsatbothinstitutions.Hewas
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pu honored as ChemPubSoc Europe Fellow (2018, Liverpool).
s://
p
htt
n
0 o Dr Anna S. Balueva graduated from Kazan
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0 StateUniversityin1984.Sincethattime,she
2
pril occupied research positions in A.E. Arbuzov
A Institute of Organic and Physical Chemistry
4
on 1 KSC RAS (IOPC), Kazan. Since 2000 she
d has been a senior researcher of the labora-
e
sh tory of organophosphorus ligands of IOPC.
ubli She received a PhD degree in 1988 under
P
the supervision of DrSci. O. A. Erastov. Her
researchinterestsincludesthesyntheticand
coordination chemistry of functionalized ter-
tiaryphosphines(inparticularP,N-containing
hetero- and macrocycles).
viii | OrganophosphorusChem.,2020,49,viii–xvi
(cid:2)c TheRoyalSocietyofChemistry2020
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Goutam Brahmachari, after receiving his
PhD in 1997 at Visva-Bharati University
(India) joined his alma mater the very next
year and currently holds the position of
a full professor of chemistry since 2011.
Research interests of his group include
green chemistry, organic synthesis, and
8 medicinal chemistry of natural and natural
0
P0 product-inspired synthetic molecules. With
F
1- more than 21 years of experience in both
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94 teaching and research, he has produced
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80 more than 200 scientific publications
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17 including original research papers, review
8
97 articles,booksandinvitedbookchaptersinthefieldofnaturalproducts
9/
3 andgreenchemistry.Hehasalreadyauthored/edited25booksandmore
0
1
0. than40bookchapterssofarpublishedbyinternationallyreputedmajor
1
oi: presses. He is the Series Editor of the Elsevier Book Series ‘Natural
d
g | ProductDrugDiscovery’.Prof.BrahmachariisaFellowoftheRoyalSociety
or of Chemistry, a Who’s Who in the World Listee, and also a recipient of
c.
s
s.r AcademicBrillianceAward2015(ExcellenceinResearch),DrKalamBest
b
u Teaching Faculty Award-2017 and INSA (Indian National Science Acad-
p
s:// emy) Teachers Award-2019.
p
htt
n
o
0
02 M´ario J. F. Calvete is currently Assistant
2
pril Professor at the University of Coimbra. He
A obtained his PhD in Natural Sciences-
4
1 Organic Chemistry in 2004, from the
d on Eberhard-Karls University of Tu¨bingen-
e
sh Germany, supervised by Michael Hanack, on
ubli the synthesis of phthalocyanine derivatives
P
forNonlinearOptics.Afterapostdoctoralstay
at Tu¨bingen (2004–2006), he returned to
Portugal as post-doc researcher at the Uni-
versity ofAveiro,workingonthesynthesis of
porphyrin(cid:3)phthalocyanine dyads and then
at the University of Coimbra (2007–2010).
In 2010 he was appointed Auxiliary Researcher at the University of
Coimbra, a position he held until 2019. His current research interests
areintetrapyrrolicmacrocycleandotherheterocyclicsdesignandtheiruse
in homogeneous/heterogeneous catalysis, theranostics and light-driven
applications. He is author of ca. 85 peer-reviewed papers, 2 books and
13 book chapters.
OrganophosphorusChem.,2020,49,viii–xvi | ix
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RuiM.B.CarrilhoisanAuxiliaryResearcher
at University of Coimbra. He obtained his
PhD diploma in Chemistry in 2014 from
University of Coimbra, supervised by M. M.
Pereira and L. Koll´ar, focused on the devel-
opmentoftervalentphosphorusligandsand
metalcomplexesforapplicationincatalysis.
8 During 2014, he worked as a post-doc
0
P0 researcher in the pharmaceutical spin-off
F
1- Luzitin SA, on the synthesis of new photo-
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94 sensitizers for application in photodynamic
1
80 therapy and diagnosis. Since 2015, he has
8
17 worked on the development of catalytic
8
9/97 processesforCO2activation.Heisauthorofca.25peer-reviewedpapers
3 and 8 book chapters.
0
1
0.
1
oi:
d
g | Amit Chakraborty obtained his BSc degree
or from the Suri Vidyasagar College, Burdwan
c.
s
s.r University, West Bengal, India, in 2007 and
b
u MSc degree in 2009 in inorganic chemistry
p
s:// fromIndianInstituteofTechnologyKanpur,
p
htt Kanpur, India. He completed his PhD at
n
o Indian Institute of Technology Kanpur,
0
02 Kanpur, India, under the supervision of
2
pril Prof. V. Chandrasekhar in 2015. He briefly
A worked as a postdoctoral research associate
4
1 at the National Institute of Science Edu-
d on cation and Research(NISER), Bhubaneswar,
e
sh India. Currently he is a National Post-
ubli doctoral Fellow at the Tata Institute of Fundamental Research Hydera-
P
bad. His research interests include molecular magnetism, transition
metal/lanthanide complexes, and design of unusual ligands and in new
molecular materials.
x | OrganophosphorusChem.,2020,49,viii–xvi