Literature DB >> 24890009

Selective functionalization of P₄ by metal-mediated C-P bond formation.

Sebastian Heinl1, Sabine Reisinger, Christoph Schwarzmaier, Michael Bodensteiner, Manfred Scheer.   

Abstract

A new and selective one-step synthesis was developed for the first activation stage of white phosphorus by organic radicals. The reactions of NaCp(R) with P4 in the presence of pan class="Gene">CuX or FeBr3 leads to the clean formation of organic substituted P4 butterfly compounds Cp(R)2P4 (Cp(R): Cp(BIG)=C5(4-nBuC6H4)5 (1 a), Cp'''=C5H2tBu3 (1 b), Cp*=C5Me5 (1 c) und Cp(4iPr)=C5HiPr4 (1 d)). The reaction proceeds via the activation of P4 by Cp(R) radicals mediated by transition metals. The newly formed organic derivatives of P4 have been comprehensively characterized by NMR spectroscopy and X-ray crystallography.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  P4 activation; organophosphorus compounds; phosphorus; radicals

Year:  2014        PMID: 24890009     DOI: 10.1002/anie.201403295

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  9 in total

1.  Activation of white phosphorus by low-valent group 5 complexes: formation and reactivity of cyclo-P4 inverted sandwich compounds.

Authors:  Clément Camp; Laurent Maron; Robert G Bergman; John Arnold
Journal:  J Am Chem Soc       Date:  2014-12-03       Impact factor: 15.419

2.  Facile storage and release of white phosphorus and yellow arsenic.

Authors:  Andreas E Seitz; Felix Hippauf; Werner Kremer; Stefan Kaskel; Manfred Scheer
Journal:  Nat Commun       Date:  2018-01-24       Impact factor: 14.919

3.  A family of cis-macrocyclic diphosphines: modular, stereoselective synthesis and application in catalytic CO2/ethylene coupling.

Authors:  Ioana Knopf; Daniel Tofan; Dirk Beetstra; Abdulaziz Al-Nezari; Khalid Al-Bahily; Christopher C Cummins
Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

4.  Metalate-Mediated Functionalization of P4 by Trapping Anionic [Cp*Fe(CO)21-P4)]- with Lewis Acids.

Authors:  Jaap E Borger; Maarten K Jongkind; Andreas W Ehlers; Martin Lutz; J Chris Slootweg; Koop Lammertsma
Journal:  ChemistryOpen       Date:  2017-03-23       Impact factor: 2.911

Review 5.  Functionalization of P4 through Direct P-C Bond Formation.

Authors:  Jaap E Borger; Andreas W Ehlers; J Chris Slootweg; Koop Lammertsma
Journal:  Chemistry       Date:  2017-07-27       Impact factor: 5.236

Review 6.  Transition-Metal-Mediated Functionalization of White Phosphorus.

Authors:  Christian M Hoidn; Daniel J Scott; Robert Wolf
Journal:  Chemistry       Date:  2020-11-18       Impact factor: 5.236

7.  Bulking up CpBIG: A Penta-Terphenyl Cyclopentadienyl Ligand.

Authors:  Gabriele Hierlmeier; Robert Wolf
Journal:  Organometallics       Date:  2022-03-15       Impact factor: 3.876

8.  Binding, Release and Functionalization of Intact Pnictogen Tetrahedra Coordinated to Dicopper Complexes.

Authors:  Martin Piesch; Amélie Nicolay; Maria Haimerl; Michael Seidl; Gábor Balázs; T Don Tilley; Manfred Scheer
Journal:  Chemistry       Date:  2022-06-23       Impact factor: 5.020

9.  Direct functionalization of white phosphorus with anionic dicarbenes and mesoionic carbenes: facile access to 1,2,3-triphosphol-2-ides.

Authors:  Dennis Rottschäfer; Sebastian Blomeyer; Beate Neumann; Hans-Georg Stammler; Rajendra S Ghadwal
Journal:  Chem Sci       Date:  2019-10-18       Impact factor: 9.825

  9 in total

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