Organophosphorus chemistry

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Editor: Prof. Paul R. Hanson
University of Kansas
 
Organophosphorus compounds are ubiquitous in nature, and due to their innate chemical properties, serve a fundamental role in a number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new heights. This Thematic Series covers topics that range from new synthetic methods and phosphorus-based ligands in asymmetric catalysis to bisphosphonates as promising enzyme inhibitors.
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Organophosphorus chemistry

  • Paul R. Hanson

Beilstein J. Org. Chem. 2014, 10, 2087–2088, doi:10.3762/bjoc.10.217

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Published 04 Sep 2014

Cyclic phosphonium ionic liquids

  • Sharon I. Lall-Ramnarine,
  • Joshua A. Mukhlall,
  • James F. Wishart,
  • Robert R. Engel,
  • Alicia R. Romeo,
  • Masao Gohdo,
  • Sharon Ramati,
  • Marc Berman and
  • Sophia N. Suarez

Beilstein J. Org. Chem. 2014, 10, 271–275, doi:10.3762/bjoc.10.22

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Published 24 Jan 2014

Phosphinate-containing heterocycles: A mini-review

  • Olivier Berger and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

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Review
Published 27 Mar 2014

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

  • Michał Górny vel Górniak,
  • Anna Czernicka,
  • Piotr Młynarz,
  • Waldemar Balcerzak and
  • Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 741–745, doi:10.3762/bjoc.10.68

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Published 28 Mar 2014

Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines

  • Jian-bo Xie,
  • Jian Luo,
  • Timothy R. Winn,
  • David B. Cordes and
  • Guigen Li

Beilstein J. Org. Chem. 2014, 10, 746–751, doi:10.3762/bjoc.10.69

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Published 31 Mar 2014

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

  • Łukasz Górecki,
  • Artur Mucha and
  • Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

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Published 17 Apr 2014

Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

  • G. Gangadhararao,
  • Ramesh Kotikalapudi,
  • M. Nagarjuna Reddy and
  • K. C. Kumara Swamy

Beilstein J. Org. Chem. 2014, 10, 996–1005, doi:10.3762/bjoc.10.99

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Published 02 May 2014

Theoretical studies on the intramolecular cyclization of 2,4,6-t-Bu3C6H2P=C: and effects of conjugation between the P=C and aromatic moieties

  • Masaaki Yoshifuji and
  • Shigekazu Ito

Beilstein J. Org. Chem. 2014, 10, 1032–1036, doi:10.3762/bjoc.10.103

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Published 07 May 2014

Preparation of phosphines through C–P bond formation

  • Iris Wauters,
  • Wouter Debrouwer and
  • Christian V. Stevens

Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106

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Published 09 May 2014

Atherton–Todd reaction: mechanism, scope and applications

  • Stéphanie S. Le Corre,
  • Mathieu Berchel,
  • Hélène Couthon-Gourvès,
  • Jean-Pierre Haelters and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

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Published 21 May 2014

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp2)–H activation/C–O formation

  • Seohyun Shin,
  • Dongjin Kang,
  • Woo Hyung Jeon and
  • Phil Ho Lee

Beilstein J. Org. Chem. 2014, 10, 1220–1227, doi:10.3762/bjoc.10.120

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Published 23 May 2014

Synthesis of 1-[bis(trifluoromethyl)phosphine]-1’-oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates

  • Zeng-Wei Lai,
  • Rong-Fei Yang,
  • Ke-Yin Ye,
  • Hongbin Sun and
  • Shu-Li You

Beilstein J. Org. Chem. 2014, 10, 1261–1266, doi:10.3762/bjoc.10.126

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Published 30 May 2014

Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis

  • Jingran Tao,
  • Li-Mei Jin and
  • X. Peter Zhang

Beilstein J. Org. Chem. 2014, 10, 1282–1289, doi:10.3762/bjoc.10.129

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Published 04 Jun 2014

Rasta resin–triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions

  • Xuanshu Xia and
  • Patrick H. Toy

Beilstein J. Org. Chem. 2014, 10, 1397–1405, doi:10.3762/bjoc.10.143

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Published 20 Jun 2014

Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction

  • Marina Rubina,
  • William M. Sherrill,
  • Alexey Yu. Barkov and
  • Michael Rubin

Beilstein J. Org. Chem. 2014, 10, 1536–1548, doi:10.3762/bjoc.10.158

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Published 07 Jul 2014

Synthesis of isoprenoid bisphosphonate ethers through C–P bond formations: Potential inhibitors of geranylgeranyl diphosphate synthase

  • Xiang Zhou,
  • Jacqueline E. Reilly,
  • Kathleen A. Loerch,
  • Raymond J. Hohl and
  • David F. Wiemer

Beilstein J. Org. Chem. 2014, 10, 1645–1650, doi:10.3762/bjoc.10.171

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Published 18 Jul 2014

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

  • Thilo Focken and
  • Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

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Published 13 Aug 2014

Relay cross metathesis reactions of vinylphosphonates

  • Raj K. Malla,
  • Jeremy N. Ridenour and
  • Christopher D. Spilling

Beilstein J. Org. Chem. 2014, 10, 1933–1941, doi:10.3762/bjoc.10.201

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Published 19 Aug 2014

Photorelease of phosphates: Mild methods for protecting phosphate derivatives

  • Sanjeewa N. Senadheera,
  • Abraham L. Yousef and
  • Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

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Published 29 Aug 2014

P(O)R2-directed Pd-catalyzed C–H functionalization of biaryl derivatives to synthesize chiral phosphorous ligands

  • Rong-Bin Hu,
  • Hong-Li Wang,
  • Hong-Yu Zhang,
  • Heng Zhang,
  • Yan-Na Ma and
  • Shang-dong Yang

Beilstein J. Org. Chem. 2014, 10, 2071–2076, doi:10.3762/bjoc.10.215

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Published 02 Sep 2014

Chiral phosphines in nucleophilic organocatalysis

  • Yumei Xiao,
  • Zhanhu Sun,
  • Hongchao Guo and
  • Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

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Published 04 Sep 2014

A modular phosphate tether-mediated divergent strategy to complex polyols

  • Paul R. Hanson,
  • Susanthi Jayasinghe,
  • Soma Maitra,
  • Cornelius N. Ndi and
  • Rambabu Chegondi

Beilstein J. Org. Chem. 2014, 10, 2332–2337, doi:10.3762/bjoc.10.242

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Published 07 Oct 2014
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