skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Tetragonal phosphorus(V) cations as tunable and robust catalytic Lewis acids

;  [1]
  1. MIT
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
National Science Foundation (NSF)
OSTI Identifier:
Resource Type:
Journal Article
Journal Name:
Chem. Sci.
Additional Journal Information:
Journal Volume: 10; Journal Issue: (30) ; 2019
Country of Publication:
United States

Citation Formats

Gilhula, J. C., and Radosevich, A. T. Tetragonal phosphorus(V) cations as tunable and robust catalytic Lewis acids. United States: N. p., 2019. Web. doi:10.1039/C9SC02463H.
Gilhula, J. C., & Radosevich, A. T. Tetragonal phosphorus(V) cations as tunable and robust catalytic Lewis acids. United States. doi:10.1039/C9SC02463H.
Gilhula, J. C., and Radosevich, A. T. Wed . "Tetragonal phosphorus(V) cations as tunable and robust catalytic Lewis acids". United States. doi:10.1039/C9SC02463H.
title = {Tetragonal phosphorus(V) cations as tunable and robust catalytic Lewis acids},
author = {Gilhula, J. C. and Radosevich, A. T.},
abstractNote = {},
doi = {10.1039/C9SC02463H},
journal = {Chem. Sci.},
number = (30) ; 2019,
volume = 10,
place = {United States},
year = {2019},
month = {9}

Works referenced in this record:

Phosphonium Salt Organocatalysis
journal, July 2009

A Convenient Synthesis of β-Aminoesters. The Reaction of Imines with Ketene Silyl Acetals Catalyzed by Phosphonium Salts
journal, August 1989

  • Mukaiyama, Teruaki; Kashiwagi, Kouichi; Matsui, Shigekazu
  • Chemistry Letters, Vol. 18, Issue 8
  • DOI: 10.1246/cl.1989.1397

Lewis Acidity of Organofluorophosphonium Salts: Hydrodefluorination by a Saturated Acceptor
journal, September 2013

C−C Coupling of Benzyl Fluorides Catalyzed by an Electrophilic Phosphonium Cation
journal, May 2016

  • Zhu, Jiangtao; Pérez, Manuel; Stephan, Douglas W.
  • Angewandte Chemie International Edition, Vol. 55, Issue 29
  • DOI: 10.1002/anie.201603627

Catalytic Ketone Hydrodeoxygenation Mediated by Highly Electrophilic Phosphonium Cations
journal, June 2015

  • Mehta, Meera; Holthausen, Michael H.; Mallov, Ian
  • Angewandte Chemie International Edition, Vol. 54, Issue 28
  • DOI: 10.1002/anie.201502579

Catalytic reduction of amides to amines by electrophilic phosphonium cations via FLP hydrosilylation
journal, January 2016

  • Augurusa, Alessandra; Mehta, Meera; Perez, Manuel
  • Chemical Communications, Vol. 52, Issue 82
  • DOI: 10.1039/C6CC06914B

Electrophilic Fluorophosphonium Cations in Frustrated Lewis Pair Hydrogen Activation and Catalytic Hydrogenation of Olefins
journal, July 2015

  • vom Stein, Thorsten; Peréz, Manuel; Dobrovetsky, Roman
  • Angewandte Chemie International Edition, Vol. 54, Issue 35
  • DOI: 10.1002/anie.201504109

Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis
journal, July 2014

  • Perez, M.; Caputo, C. B.; Dobrovetsky, R.
  • Proceedings of the National Academy of Sciences, Vol. 111, Issue 30
  • DOI: 10.1073/pnas.1407484111

Phosphorus Lewis acids: emerging reactivity and applications in catalysis
journal, January 2016

  • Bayne, J. M.; Stephan, D. W.
  • Chemical Society Reviews, Vol. 45, Issue 4
  • DOI: 10.1039/C5CS00516G

Lewis Superacids: Classifications, Candidates, and Applications
journal, October 2018

[Sb(C 6 F 5 ) 4 ][B(C 6 F 5 ) 4 ]: An Air Stable, Lewis Acidic Stibonium Salt That Activates Strong Element-Fluorine Bonds
journal, June 2014

  • Pan, Baofei; Gabbaï, François P.
  • Journal of the American Chemical Society, Vol. 136, Issue 27
  • DOI: 10.1021/ja505214m

Digging the Sigma-Hole of Organoantimony Lewis Acids by Oxidation
journal, September 2018

  • Yang, Mengxi; Tofan, Daniel; Chen, Chang-Hong
  • Angewandte Chemie International Edition, Vol. 57, Issue 42
  • DOI: 10.1002/anie.201808551

Phosphorous( v ) Lewis acids: water/base tolerant P 3 -trimethylated trications
journal, January 2018

  • Bayne, J. M.; Fasano, V.; Szkop, K. M.
  • Chemical Communications, Vol. 54, Issue 88
  • DOI: 10.1039/C8CC06564K

Air- and water-stable Lewis acids: synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations
journal, January 2018

  • Fasano, V.; LaFortune, J. H. W.; Bayne, J. M.
  • Chemical Communications, Vol. 54, Issue 6
  • DOI: 10.1039/C7CC09128A

Catalytic Hydrodefluorination of C−F Bonds by an Air-Stable P III Lewis Acid
journal, April 2018

  • Chitnis, Saurabh S.; Krischer, Felix; Stephan, Douglas W.
  • Chemistry - A European Journal, Vol. 24, Issue 25
  • DOI: 10.1002/chem.201801305

Phosphorus Coordination Chemistry in Catalysis: Air Stable P(III)-Dications as Lewis Acid Catalysts for the Allylation of C–F Bonds
journal, October 2018

Carbonyl and olefin hydrosilylation mediated by an air-stable phosphorus( iii ) dication under mild conditions
journal, January 2019

  • Andrews, Ryan J.; Chitnis, Saurabh S.; Stephan, Douglas W.
  • Chemical Communications, Vol. 55, Issue 39
  • DOI: 10.1039/C9CC02460C

Biphilic Organophosphorus-Catalyzed Intramolecular C sp 2 –H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations
journal, February 2018

  • Nykaza, Trevor V.; Ramirez, Antonio; Harrison, Tyler S.
  • Journal of the American Chemical Society, Vol. 140, Issue 8
  • DOI: 10.1021/jacs.7b13803

Intermolecular Reductive C–N Cross Coupling of Nitroarenes and Boronic Acids by P III /P V ═O Catalysis
journal, October 2018

  • Nykaza, Trevor V.; Cooper, Julian C.; Li, Gen
  • Journal of the American Chemical Society, Vol. 140, Issue 45
  • DOI: 10.1021/jacs.8b10769

Reversible Intermolecular E–H Oxidative Addition to a Geometrically Deformed and Structurally Dynamic Phosphorous Triamide
journal, December 2014

  • Zhao, Wei; McCarthy, Sean M.; Lai, Ting Yi
  • Journal of the American Chemical Society, Vol. 136, Issue 50
  • DOI: 10.1021/ja510558d

P–N Cooperative Borane Activation and Catalytic Hydroboration by a Distorted Phosphorous Triamide Platform
journal, April 2017

  • Lin, Yi-Chun; Hatzakis, Emmanuel; McCarthy, Sean M.
  • Journal of the American Chemical Society, Vol. 139, Issue 16
  • DOI: 10.1021/jacs.7b02512

Nontrigonal constraint enhances 1,2-addition reactivity of phosphazenes
journal, January 2018

  • Lin, Yi-Chun; Gilhula, James C.; Radosevich, Alexander T.
  • Chemical Science, Vol. 9, Issue 18
  • DOI: 10.1039/C8SC00929E

Corroles with Group 15 Ions. 2. Synthesis and Characterization of Octaethylcorroles Containing a Phosphorus Central Atom
journal, December 2000

  • Kadish, Karl M.; Ou, Zhongping; Adamian, Victor A.
  • Inorganic Chemistry, Vol. 39, Issue 25
  • DOI: 10.1021/ic0010196

Synthesis, Structure and Properties of a Five-Coordinate Oxophosphorus(V) meso-Triphenylcorrole
journal, August 2012

  • Ghosh, Avijit; Lee, Way-Zen; Ravikanth, Mangalampalli
  • European Journal of Inorganic Chemistry, Vol. 2012, Issue 26
  • DOI: 10.1002/ejic.201200651

Intriguing Physical and Chemical Properties of Phosphorus Corroles
journal, May 2016

Synthesis, Structure, Spectroscopic, and Electrochemical Properties of Highly Fluorescent Phosphorus(V)- meso -Triarylcorroles
journal, March 2012

  • Ghosh, Avijit; Ravikanth, Mangalampalli
  • Chemistry - A European Journal, Vol. 18, Issue 20
  • DOI: 10.1002/chem.201103226

A Highly Emissive Water-Soluble Phosphorus Corrole
journal, December 2016

  • Naitana, Mario L.; Nardis, Sara; Pomarico, Giuseppe
  • Chemistry - A European Journal, Vol. 23, Issue 4
  • DOI: 10.1002/chem.201604233

Phosphorus(V) corrole: DNA binding, photonuclease activity and cytotoxicity toward tumor cells
journal, August 2016

Stabilization of hexa-coordinated P( v ) corroles by axial silyloxy groups
journal, January 2016

  • Chatterjee, Tamal; Lee, Way-Zen; Ravikanth, Mangalampalli
  • Dalton Transactions, Vol. 45, Issue 18
  • DOI: 10.1039/C6DT00842A

The global electrophilicity index as a metric for Lewis acidity
journal, January 2018

  • Jupp, Andrew R.; Johnstone, Timothy C.; Stephan, Douglas W.
  • Dalton Transactions, Vol. 47, Issue 20
  • DOI: 10.1039/C8DT01699B

Improving the Global Electrophilicity Index (GEI) as a Measure of Lewis Acidity
journal, November 2018

Nucleus-Independent Chemical Shifts:  A Simple and Efficient Aromaticity Probe
journal, January 1996

  • Schleyer, Paul von Ragué; Maerker, Christoph; Dransfeld, Alk
  • Journal of the American Chemical Society, Vol. 118, Issue 26
  • DOI: 10.1021/ja960582d

Phosphorus complex of corrole
journal, January 1998

  • Paolesse, Roberto; Boschi, Tristano; Licoccia, Silvia
  • Chemical Communications, Issue 10
  • DOI: 10.1039/a801544i

The acceptor number ? A quantitative empirical parameter for the electrophilic properties of solvents
journal, January 1975

  • Mayer, Ulrich; Gutmann, Viktor; Gerger, Wolfgang
  • Monatshefte f�r Chemie, Vol. 106, Issue 6
  • DOI: 10.1007/BF00913599

Lewis acid addticts of α,β-unsaturated carbonyl and nitrile compounds. A calorimetric study
journal, March 1982

  • Childs, Ronald F.; Mulholland, D. Lindsay; Nixon, Alan
  • Canadian Journal of Chemistry, Vol. 60, Issue 6
  • DOI: 10.1139/v82-118

The Correlation of Lewis Acidities of Silyl Triflates with Reaction Rates of Catalyzed Diels-Alder Reactions
journal, November 2011

  • Hilt, Gerhard; Nödling, Alexander
  • European Journal of Organic Chemistry, Vol. 2011, Issue 35
  • DOI: 10.1002/ejoc.201101307

Ferrocene-Stabilized Silicon Cations as Catalysts for Diels–Alder Reactions: Attempted Experimental Quantification of Lewis Acidity and ReactIR Kinetic Analysis
journal, December 2013

  • Nödling, Alexander R.; Müther, Kristine; Rohde, Volker H. G.
  • Organometallics, Vol. 33, Issue 1
  • DOI: 10.1021/om401040y

Quantitative Assessment of the Lewis Acidity of Silylium Ions
journal, July 2015

Novel B(Ar′) 2 (Ar′′) hetero-tri(aryl)boranes: a systematic study of Lewis acidity
journal, January 2016

  • Blagg, Robin J.; Simmons, Trevor R.; Hatton, Georgina R.
  • Dalton Transactions, Vol. 45, Issue 14
  • DOI: 10.1039/C5DT03854E

A Simple and Effective Method of Determining Lewis Acidity by Using Fluorescence
journal, June 2019

From B(C 6 F 5 ) 3 to B(OC 6 F 5 ) 3 :  Synthesis of (C 6 F 5 ) 2 BOC 6 F 5 and C 6 F 5 B(OC 6 F 5 ) 2 and Their Relative Lewis Acidity
journal, March 2005

  • Britovsek, George J. P.; Ugolotti, Juri; White, Andrew J. P.
  • Organometallics, Vol. 24, Issue 7
  • DOI: 10.1021/om049091p

Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
journal, January 2005

  • Weigend, Florian; Ahlrichs, Reinhart
  • Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305
  • DOI: 10.1039/b508541a

Electronic Structure of Gallium, Copper, and Nickel Complexes of Corrole. High-Valent Transition Metal Centers versus Noninnocent Ligands
journal, May 2000

  • Ghosh, Abhik; Wondimagegn, Tebikie; Parusel, Andreas B. J.
  • Journal of the American Chemical Society, Vol. 122, Issue 21
  • DOI: 10.1021/ja9943243

On a quantitative scale for Lewis acidity and recent progress in polynitrogen chemistry
journal, February 2000

Mechanisms of Substitution Reactions at Phosphorus. X. The Wittig Reaction and the Decomposition of Quaternary Phosphonium Hydroxides
journal, June 1964

  • McEwen, William E.; Kumli, Karl F.; Blade-Font, Arturo.
  • Journal of the American Chemical Society, Vol. 86, Issue 12
  • DOI: 10.1021/ja01066a017

Lewis Acids:  From Conventional Homogeneous to Green Homogeneous and Heterogeneous Catalysis
journal, November 2003

  • Corma, Avelino; García, Hermenegildo
  • Chemical Reviews, Vol. 103, Issue 11
  • DOI: 10.1021/cr030680z

Lewis Acid Catalyzed Formation of Tetrahydroquinolines via an Intramolecular Redox Process
journal, January 2009

  • Murarka, Sandip; Zhang, Chen; Konieczynska, Marlena D.
  • Organic Letters, Vol. 11, Issue 1
  • DOI: 10.1021/ol802519r

Metal-Free Deoxygenation of Carbohydrates
journal, January 2014

  • Adduci, Laura L.; McLaughlin, Matthew P.; Bender, Trandon A.
  • Angewandte Chemie International Edition, Vol. 53, Issue 6
  • DOI: 10.1002/anie.201306864