Adaptable ligand donor strength: tracking transannular bond interactions in tris(2-pyridylmethyl)-azaphosphatrane (TPAP)
Abstract
Flexible ligands that can adapt their donor strength have enabled unique reactivity in a wide range of inorganic complexes. Most examples are composed of flexible multi-dentate ligands containing a donor that can vary its interaction through its distance to the metal center. We describe an alternative type of adaptable ligand interaction in the neutral multi-dentate ligand tris(2-pyridylmethyl)-azaphosphatrane (TPAP), which contains a proazaphosphatrane unit. Prozaphosphatranes are intrinsically strong phosphorus donors; upon coordination to more Lewis acidic atoms the phosphorus can accept additional electron density from a tertiary nitrogen to form a transannular bond, increasing its donor strength. An experimental and computational investigation of the varying degree of transannular interaction in TPAP when coordinated to late transition metals is reported in this paper. The synthesis and characterization of the complexes M(TPAP), where M = Co(I)Cl, Ni(0)(1,5-cyclooctadiene), Ni(II)(CH3CN)(BF4)2, Pd(II)(CH3CN)(BF4)2, or Pt(II)Cl(PF6) is described. Structural characterization and density functional theory calculation of these complexes, along with the previously reported [Co(II)(TPAP)(CH3CN)](BF4)2 establish significant increases in the degree of transannular interaction of the proazaphosphatrane unit when coordinated to more electron deficient metal ions.
- Authors:
-
- Univ. of California, Irvine, CA (United States)
- Univ. of Minnesota, Minneapolis, MN (United States)
- Publication Date:
- Research Org.:
- Univ. of California, Irvine, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1611734
- Alternate Identifier(s):
- OSTI ID: 1473721
- Grant/Contract Number:
- SC0012150
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Dalton Transactions
- Additional Journal Information:
- Journal Volume: 47; Journal Issue: 39; Journal ID: ISSN 1477-9226
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Chemistry
Citation Formats
Thammavongsy, Zachary, Cunningham, Drew W., Sutthirat, Natwara, Eisenhart, Reed J., Ziller, Joseph W., and Yang, Jenny Y. Adaptable ligand donor strength: tracking transannular bond interactions in tris(2-pyridylmethyl)-azaphosphatrane (TPAP). United States: N. p., 2018.
Web. doi:10.1039/c8dt03180k.
Thammavongsy, Zachary, Cunningham, Drew W., Sutthirat, Natwara, Eisenhart, Reed J., Ziller, Joseph W., & Yang, Jenny Y. Adaptable ligand donor strength: tracking transannular bond interactions in tris(2-pyridylmethyl)-azaphosphatrane (TPAP). United States. https://doi.org/10.1039/c8dt03180k
Thammavongsy, Zachary, Cunningham, Drew W., Sutthirat, Natwara, Eisenhart, Reed J., Ziller, Joseph W., and Yang, Jenny Y. Fri .
"Adaptable ligand donor strength: tracking transannular bond interactions in tris(2-pyridylmethyl)-azaphosphatrane (TPAP)". United States. https://doi.org/10.1039/c8dt03180k. https://www.osti.gov/servlets/purl/1611734.
@article{osti_1611734,
title = {Adaptable ligand donor strength: tracking transannular bond interactions in tris(2-pyridylmethyl)-azaphosphatrane (TPAP)},
author = {Thammavongsy, Zachary and Cunningham, Drew W. and Sutthirat, Natwara and Eisenhart, Reed J. and Ziller, Joseph W. and Yang, Jenny Y.},
abstractNote = {Flexible ligands that can adapt their donor strength have enabled unique reactivity in a wide range of inorganic complexes. Most examples are composed of flexible multi-dentate ligands containing a donor that can vary its interaction through its distance to the metal center. We describe an alternative type of adaptable ligand interaction in the neutral multi-dentate ligand tris(2-pyridylmethyl)-azaphosphatrane (TPAP), which contains a proazaphosphatrane unit. Prozaphosphatranes are intrinsically strong phosphorus donors; upon coordination to more Lewis acidic atoms the phosphorus can accept additional electron density from a tertiary nitrogen to form a transannular bond, increasing its donor strength. An experimental and computational investigation of the varying degree of transannular interaction in TPAP when coordinated to late transition metals is reported in this paper. The synthesis and characterization of the complexes M(TPAP), where M = Co(I)Cl, Ni(0)(1,5-cyclooctadiene), Ni(II)(CH3CN)(BF4)2, Pd(II)(CH3CN)(BF4)2, or Pt(II)Cl(PF6) is described. Structural characterization and density functional theory calculation of these complexes, along with the previously reported [Co(II)(TPAP)(CH3CN)](BF4)2 establish significant increases in the degree of transannular interaction of the proazaphosphatrane unit when coordinated to more electron deficient metal ions.},
doi = {10.1039/c8dt03180k},
journal = {Dalton Transactions},
number = 39,
volume = 47,
place = {United States},
year = {Fri Sep 14 00:00:00 EDT 2018},
month = {Fri Sep 14 00:00:00 EDT 2018}
}
Web of Science
Works referenced in this record:
Tuning of Metal Complex Electronics and Reactivity by Remote Lewis Acid Binding to π-Coordinated Pyridine Diphosphine Ligands
journal, August 2015
- Horak, Kyle T.; VanderVelde, David G.; Agapie, Theodor
- Organometallics, Vol. 34, Issue 19
Comparisons of lanthanide/actinide +2 ions in a tris(aryloxide)arene coordination environment
journal, January 2017
- Fieser, Megan E.; Palumbo, Chad T.; La Pierre, Henry S.
- Chem. Sci., Vol. 8, Issue 11
N 2 Functionalization at Iron Metallaboratranes
journal, November 2011
- Moret, Marc-Etienne; Peters, Jonas C.
- Journal of the American Chemical Society, Vol. 133, Issue 45
Superbases in Confined Space: Control of the Basicity and Reactivity of the Proton Transfer
journal, November 2013
- Chatelet, Bastien; Gornitzka, Heinz; Dufaud, Véronique
- Journal of the American Chemical Society, Vol. 135, Issue 49
Dinitrogen Activation at Iron and Cobalt Metallalumatranes
journal, July 2013
- Rudd, P. Alex; Planas, Nora; Bill, Eckhard
- European Journal of Inorganic Chemistry, Vol. 2013, Issue 22-23
Catalytic conversion of nitrogen to ammonia by an iron model complex
journal, September 2013
- Anderson, John S.; Rittle, Jonathan; Peters, Jonas C.
- Nature, Vol. 501, Issue 7465
A synthetic and mechanistic investigation into the cobalt( i ) catalyzed amination of aryl halides
journal, January 2014
- Brennan, Marshall R.; Kim, Dongyoung; Fout, Alison R.
- Chem. Sci., Vol. 5, Issue 12
Arene non-innocence in dinuclear complexes of Fe, Co, and Ni supported by a para-terphenyl diphosphine
journal, January 2014
- Horak, Kyle T.; Velian, Alexandra; Day, Michael W.
- Chem. Commun., Vol. 50, Issue 34
One-Pot Sequential N and C Arylations: An Efficient Methodology for the Synthesis oftrans 4-N,N-Diaryl Aminostilbenes
journal, May 2005
- Nandakumar, Mecheril V.; Verkade, John G.
- Angewandte Chemie International Edition, Vol. 44, Issue 20
A Highly Effective Catalyst System for the Pd-Catalyzed Amination of Vinyl Bromides and Chlorides
journal, September 2005
- Venkat Reddy, Chinta Reddy; Urgaonkar, Sameer; Verkade, John G.
- Organic Letters, Vol. 7, Issue 20
Combination of Redox-Active Ligand and Lewis Acid for Dioxygen Reduction with π-Bound Molybdenum−Quinonoid Complexes
journal, January 2015
- Henthorn, Justin T.; Lin, Sibo; Agapie, Theodor
- Journal of the American Chemical Society, Vol. 137, Issue 4
Synthesis and Photoelectron Spectroscopic Studies of N(CH 2 CH 2 NMe) 3 PE (E = O, S, NH, CH 2 )
journal, February 2006
- Kárpáti, Tamás; Veszprémi, Tamás; Thirupathi, Natesan
- Journal of the American Chemical Society, Vol. 128, Issue 5
Pd 2 (dba) 3 /P( i -BuNCH 2 CH 2 ) 3 N-Catalyzed Stille Cross-Coupling of Aryl Chlorides
journal, April 2004
- Su, Weiping; Urgaonkar, Sameer; Verkade, John G.
- Organic Letters, Vol. 6, Issue 9
Trinuclear Nickel Complexes with Metal–Arene Interactions Supported by Tris- and Bis(phosphinoaryl)benzene Frameworks
journal, November 2013
- Suseno, Sandy; Horak, Kyle T.; Day, Michael W.
- Organometallics, Vol. 32, Issue 23
The unusually robust phosphorus-hydrogen bond in the novel cation [cyclic] HP(NMeCH2CH2)3N+
journal, April 1989
- Lensink, C.; Xi, S. K.; Daniels, L. M.
- Journal of the American Chemical Society, Vol. 111, Issue 9
NMR nomenclature. Nuclear spin properties and conventions for chemical shifts(IUPAC Recommendations 2001)
journal, January 2001
- Harris, Robin K.; Becker, Edwin D.; Cabral de Menezes, Sonia M.
- Pure and Applied Chemistry, Vol. 73, Issue 11
New Chemistry of ZP(RNCH 2 CH 2 ) 3 N Systems
journal, January 1999
- Kisanga, Philip; Mcleod, Dale; Liu, Xiaodong
- Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 144, Issue 1
Aryl Ether Cleavage by Group 9 and 10 Transition Metals: Stoichiometric Studies of Selectivity and Mechanism
journal, October 2015
- Edouard, Guy A.; Kelley, Paul; Herbert, David E.
- Organometallics, Vol. 34, Issue 21
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007
- Zhao, Yan; Truhlar, Donald G.
- Theoretical Chemistry Accounts, Vol. 120, Issue 1-3
P[( S , S , S )-PhHMeCNCH 2 CH 2 ] 3 N: A New Chiral 31 P and 1 H NMR Spectroscopic Reagent for the Direct Determination of e e Values of Chiral Azides
journal, February 2000
- Liu, Xiaodong; Ilankumaran, Palanichamy; Guzei, Ilia A.
- The Journal of Organic Chemistry, Vol. 65, Issue 3
Uranium-mediated electrocatalytic dihydrogen production from water
journal, January 2016
- Halter, Dominik P.; Heinemann, Frank W.; Bachmann, Julien
- Nature, Vol. 530, Issue 7590
Encaging the Verkade’s Superbases: Thermodynamic and Kinetic Consequences
journal, February 2011
- Raytchev, Pascal Dimitrov; Martinez, Alexandre; Gornitzka, Heinz
- Journal of the American Chemical Society, Vol. 133, Issue 7
Unusually Lewis basic Pro-azaphosphatranes
journal, November 1991
- Laramay, Mary A. H.; Verkade, John G.
- Zeitschrift f�r anorganische und allgemeine Chemie, Vol. 605, Issue 1
Nickel Hydrides Supported by a Non-Innocent Diphosphine Arene Pincer: Mechanistic Studies of Nickel−Arene H-Migration and Partial Arene Hydrogenation
journal, March 2011
- Lin, Sibo; Day, Michael W.; Agapie, Theodor
- Journal of the American Chemical Society, Vol. 133, Issue 11
Fe-N2/CO complexes that model a possible role for the interstitial C atom of FeMo-cofactor (FeMoco)
journal, September 2013
- Rittle, J.; Peters, J. C.
- Proceedings of the National Academy of Sciences, Vol. 110, Issue 40
Strongly Basic Proazaphosphatranes: P (EtNCH 2 CH 2 ) 3 N and P ( iso -PrNCH 2 CH 2 ) 3 N
journal, September 1995
- Wróblewski, Andrzej E.; Pinkas, Jiri; Verkade, John G.
- Main Group Chemistry, Vol. 1, Issue 1
Carbon dioxide cleavage by a Ni 2 complex supported by a binucleating bis(N-heterocyclic carbene) framework
journal, December 2014
- Tsui, Emily Y.; Agapie, Theodor
- Polyhedron, Vol. 84
Zinc and Magnesium Catalysts for the Hydrosilylation of Carbon Dioxide
journal, December 2017
- Rauch, Michael; Parkin, Gerard
- Journal of the American Chemical Society, Vol. 139, Issue 50
Selective and Efficient Syntheses of Perhydro-1,3,5-triazine-2,4,6-triones and Carbodiimides from Isocyanates Using ZP(MeNCH2CH2)3N Catalysts
journal, August 1994
- Tang, Jiansheng; Mohan, Thyagarajan; Verkade, John G.
- The Journal of Organic Chemistry, Vol. 59, Issue 17
Pd/P(i-BuNCH2CH2)3N: an efficient catalyst for Suzuki cross-coupling of aryl bromides and chlorides with arylboronic acids
journal, December 2002
- Urgaonkar, Sameer; Nagarajan, M.; Verkade, J. G.
- Tetrahedron Letters, Vol. 43, Issue 49
Synthesis and structural features of new sterically hindered azaphosphatrane systems: ZP(RNCH2CH2)3N
journal, June 1999
- Liu, X.; Bai, Y.; Verkade, J. G.
- Journal of Organometallic Chemistry, Vol. 582, Issue 1
The classification and representation of main group element compounds that feature three-center four-electron interactions
journal, January 2016
- Green, Malcolm L. H.; Parkin, Gerard
- Dalton Transactions, Vol. 45, Issue 47
Evaluating Molecular Cobalt Complexes for the Conversion of N 2 to NH 3
journal, May 2015
- Del Castillo, Trevor J.; Thompson, Niklas B.; Suess, Daniel L. M.
- Inorganic Chemistry, Vol. 54, Issue 19
Tris[(1-isopropylbenzimidazol-2-yl)dimethylsilyl]methyl metal complexes, [Tism PriBenz ]M: a new class of metallacarbatranes, isomerization to a tris(N-heterocyclic carbene) derivative, and evidence for an inverted ligand field
journal, January 2017
- Ruccolo, Serge; Rauch, Michael; Parkin, Gerard
- Chemical Science, Vol. 8, Issue 6
Tuning Nickel with Lewis Acidic Group 13 Metalloligands for Catalytic Olefin Hydrogenation
journal, September 2015
- Cammarota, Ryan C.; Lu, Connie C.
- Journal of the American Chemical Society, Vol. 137, Issue 39
Bridgehead-bridgehead communication in untransannulated phosphatrane ZP(ECH2CH2)3N systems
journal, June 1990
- Xi, S. K.; Schmidt, H.; Lensink, C.
- Inorganic Chemistry, Vol. 29, Issue 12
Theoretical Study of the Structure and Bonding in Phosphatrane Molecules
journal, May 2004
- Galasso, V.
- The Journal of Physical Chemistry A, Vol. 108, Issue 20
Stepwise transannular bond formation between the bridgehead atoms in Z-P(MeNCH2CH2)3N systems
journal, April 1992
- Tang, J. S.; Laramay, M. A. H.; Young, V.
- Journal of the American Chemical Society, Vol. 114, Issue 8
Synthesis, Structure, and Reactivity of a Terminal Magnesium Hydride Compound with a Carbatrane Motif, [Tism Pr i Benz ]MgH: A Multifunctional Catalyst for Hydrosilylation and Hydroboration
journal, September 2017
- Rauch, Michael; Ruccolo, Serge; Parkin, Gerard
- Journal of the American Chemical Society, Vol. 139, Issue 38
Unusual Phosphoryl Donor Properties of OP(MeNCH 2 CH 2 ) 3 N
journal, October 1998
- Liu, Xiao-Dong; Verkade, John G.
- Inorganic Chemistry, Vol. 37, Issue 20
Stable Dihydrogen Complexes of Cobalt(−I) Suggest an Inverse trans -Influence of Lewis Acidic Group 13 Metalloligands
journal, May 2017
- Vollmer, Matthew V.; Xie, Jing; Lu, Connie C.
- Journal of the American Chemical Society, Vol. 139, Issue 19
Modulation of Zn–C Bond Lengths Induced by Ligand Architecture in Zinc Carbatrane Compounds
journal, October 2016
- Ruccolo, Serge; Sattler, Wesley; Rong, Yi
- Journal of the American Chemical Society, Vol. 138, Issue 44
P(RNCH 2 CH 2 ) 3 N: Efficient Catalysts for Transesterifications, Acylations, and Deacylations
journal, April 1999
- Ilankumaran, Palanichamy; Verkade, J. G.
- The Journal of Organic Chemistry, Vol. 64, Issue 9
Tuning the Si–N Interaction in Metalated Oligosilanylsilatranes
journal, March 2017
- Aghazadeh Meshgi, Mohammad; Zitz, Rainer; Walewska, Małgorzata
- Organometallics, Vol. 36, Issue 7
Use of the Nonionic Superbase P(MeNCH 2 CH 2 ) 3 N in the Selective Monoalkylation of Active-Methylene Compounds
journal, May 1998
- Arumugam, Subramaniam; McLeod, Dale; Verkade, John G.
- The Journal of Organic Chemistry, Vol. 63, Issue 11
P( i -BuNCH 2 CH 2 ) 3 N: An Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides
journal, January 2003
- Urgaonkar, Sameer; Nagarajan, M.; Verkade, J. G.
- The Journal of Organic Chemistry, Vol. 68, Issue 2
Free and Polymer-Bound Tricyclic Azaphosphatranes HP(RNCH 2 CH 2 ) 3 N + : Procatalysts in Dehydrohalogenations and Debrominations with NaH
journal, June 1999
- Liu, Xiaodong; Verkade, John G.
- The Journal of Organic Chemistry, Vol. 64, Issue 13
Synthesis and reactivity patterns of new proazaphosphatranes and quasi-azaphosphatranes ZP(MeNCH2CH2)3N
journal, March 1993
- Tang, Jian Sheng; Verkade, John G.
- Journal of the American Chemical Society, Vol. 115, Issue 5
p K a Measurements of P(RNCH 2 CH 3 ) 3 N
journal, August 2000
- Kisanga, Philip B.; Verkade, John G.; Schwesinger, Reinhard
- The Journal of Organic Chemistry, Vol. 65, Issue 17
Theoretical Investigation of Azaphosphatrane Bases
journal, December 1994
- Windus, Theresa L.; Schmidt, Michael W.; Gordon, Mark S.
- Journal of the American Chemical Society, Vol. 116, Issue 25
Heterometallic Effects in Trinuclear Complexes Supported by p -Terphenyl Diphosphine Ligands
journal, June 2015
- Horak, Kyle T.; Lin, Sibo; Rittle, Jonathan
- Organometallics, Vol. 34, Issue 18
P(RNCH 2 CH 2 ) 3 N-Catalyzed Synthesis of β-Hydroxy Nitriles
journal, April 1999
- Kisanga, Philip; McLeod, Dale; D'S, Bosco
- The Journal of Organic Chemistry, Vol. 64, Issue 9
Electronic and steric Tolman parameters for proazaphosphatranes, the superbase core of the tri(pyridylmethyl)azaphosphatrane (TPAP) ligand
journal, January 2016
- Thammavongsy, Zachary; Kha, Ivy M.; Ziller, Joseph W.
- Dalton Transactions, Vol. 45, Issue 24
Mechanism of Molybdenum-Mediated Carbon Monoxide Deoxygenation and Coupling: Mono- and Dicarbyne Complexes Precede C–O Bond Cleavage and C–C Bond Formation
journal, December 2016
- Buss, Joshua A.; Agapie, Theodor
- Journal of the American Chemical Society, Vol. 138, Issue 50
Dioxygen Reduction by a Pd(0)–Hydroquinone Diphosphine Complex
journal, March 2016
- Horak, Kyle T.; Agapie, Theodor
- Journal of the American Chemical Society, Vol. 138, Issue 10
Structural variation in copper( i ) complexes with pyridylmethylamide ligands: structural analysis with a new four-coordinate geometry index, τ 4
journal, January 2007
- Yang, Lei; Powell, Douglas R.; Houser, Robert P.
- Dalton Trans., Issue 9
Flexibility is Key: Synthesis of a Tripyridylamine (TPA) Congener with a Phosphorus Apical Donor and Coordination to Cobalt(II)
journal, November 2015
- Thammavongsy, Zachary; Khosrowabadi Kotyk, Juliet F.; Tsay, Charlene
- Inorganic Chemistry, Vol. 54, Issue 23
Four-electron deoxygenative reductive coupling of carbon monoxide at a single metal site
journal, December 2015
- Buss, Joshua A.; Agapie, Theodor
- Nature, Vol. 529, Issue 7584
Dipalladium(I) Terphenyl Diphosphine Complexes as Models for Two-Site Adsorption and Activation of Organic Molecules
journal, October 2013
- Lin, Sibo; Herbert, David E.; Velian, Alexandra
- Journal of the American Chemical Society, Vol. 135, Issue 42
The "anomalous" basicity of P(NHCH2CH2)3N relative to P(NMeCH2CH2)3N and p(NBzCH2CH2)3N: a chemical consequence of orbital charge balance?
journal, December 1990
- Laramay, M. A. H.; Verkade, John G.
- Journal of the American Chemical Society, Vol. 112, Issue 25
Photoelectron Spectra and Structures of Proazaphosphatranes
journal, January 1996
- Nyulászi, László; Veszprémi, Tamás; D'S, Bosco A.
- Inorganic Chemistry, Vol. 35, Issue 21
A Bimetallic Nickel–Gallium Complex Catalyzes CO 2 Hydrogenation via the Intermediacy of an Anionic d 10 Nickel Hydride
journal, September 2017
- Cammarota, Ryan C.; Vollmer, Matthew V.; Xie, Jing
- Journal of the American Chemical Society, Vol. 139, Issue 40
P( i -BuNCH 2 CH 2 ) 3 N: An Efficient Ligand for the Direct α-Arylation of Nitriles with Aryl Bromides
journal, October 2003
- You, Jingsong; Verkade, John G.
- The Journal of Organic Chemistry, Vol. 68, Issue 21
A New Tripodal Ligand System with Steric and Electronic Modularity for Uranium Coordination Chemistry
journal, October 2009
- Bart, Suzanne C.; Heinemann, Frank W.; Anthon, Christian
- Inorganic Chemistry, Vol. 48, Issue 19
Reversible Halide-Modulated Nickel-Nickel Bond Cleavage: Metal-Metal Bonds as Design Elements for Molecular Devices
journal, June 2011
- Chao, Steven T.; Lara, Nadia C.; Lin, Sibo
- Angewandte Chemie International Edition, Vol. 50, Issue 33
Molybdenum Catalyzed Ammonia Borane Dehydrogenation: Oxidation State Specific Mechanisms
journal, July 2014
- Buss, Joshua A.; Edouard, Guy A.; Cheng, Christine
- Journal of the American Chemical Society, Vol. 136, Issue 32
Modulation of Proton-Coupled Electron Transfer through Molybdenum–Quinonoid Interactions
journal, May 2016
- Henthorn, Justin T.; Agapie, Theodor
- Inorganic Chemistry, Vol. 55, Issue 11
Cadmium Compounds with an [N 3 C] Atrane Motif: Evidence for the Generation of a Cadmium Hydride Species
journal, November 2016
- Chakrabarti, Neena; Ruccolo, Serge; Parkin, Gerard
- Inorganic Chemistry, Vol. 55, Issue 23
Conversion of Fe–NH 2 to Fe–N 2 with release of NH 3
journal, December 2012
- Anderson, John S.; Moret, Marc-Etienne; Peters, Jonas C.
- Journal of the American Chemical Society, Vol. 135, Issue 2
Catalytic Reduction of N 2 to NH 3 by an Fe–N 2 Complex Featuring a C-Atom Anchor
journal, January 2014
- Creutz, Sidney E.; Peters, Jonas C.
- Journal of the American Chemical Society, Vol. 136, Issue 3
Synthesis of Gold(I) Complexes Bearing Verkade's Superbases: Synthesis of Gold(I) Complexes Bearing Verkade's Superbases
journal, October 2017
- Chatelet, Bastien; Nava, Paola; Clavier, Herve
- European Journal of Inorganic Chemistry, Vol. 2017, Issue 37
A Polar Copper–Boron One-Electron σ-Bond
journal, March 2013
- Moret, Marc-Etienne; Zhang, Limei; Peters, Jonas C.
- Journal of the American Chemical Society, Vol. 135, Issue 10
Stereo- and Regioselective Pt(DVDS)/P( i BuNCH 2 CH 2 ) 3 N-Catalyzed Hydrosilylation of Terminal Alkynes
journal, May 2005
- Aneetha, Halikhedkar; Wu, Wei; Verkade, John G.
- Organometallics, Vol. 24, Issue 11
One-Pot Sequential N and C Arylations: An Efficient Methodology for the Synthesis oftrans 4-N,N-Diaryl Aminostilbenes
journal, May 2005
- Nandakumar, Mecheril V.; Verkade, John G.
- Angewandte Chemie, Vol. 117, Issue 20
Reversible Halide-Modulated Nickel-Nickel Bond Cleavage: Metal-Metal Bonds as Design Elements for Molecular Devices
journal, June 2011
- Chao, Steven T.; Lara, Nadia C.; Lin, Sibo
- Angewandte Chemie, Vol. 123, Issue 33
P(i-BuNCH2CH2)3N: An Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides.
journal, June 2003
- Urgaonkar, Sameer; Nagarajan, M.; Verkade, J. G.
- ChemInform, Vol. 34, Issue 23
P(i-BuNCH2CH2)3N: An Efficient Ligand for the Direct α-Arylation of Nitriles with Aryl Bromides.
journal, February 2004
- You, Jingsong; Verkade, John G.
- ChemInform, Vol. 35, Issue 8
Free and Polymer-Bound Tricyclic Azaphosphatranes HP(RNCH 2 CH 2 ) 3 N + : Procatalysts in Dehydrohalogenations and Debrominations with NaH.
journal, September 1999
- Liu, Xiaodong; Verkade, John G.
- The Journal of Organic Chemistry, Vol. 64, Issue 21
Pd 2 (dba) 3 /P( i -BuNCH 2 CH 2 ) 3 N-Catalyzed Stille Cross-Coupling of Aryl Chlorides
journal, November 2004
- Su, Weiping; Urgaonkar, Sameer; Verkade, John G.
- Organic Letters, Vol. 6, Issue 25
A Highly Effective Catalyst System for the Pd-Catalyzed Amination of Vinyl Bromides and Chlorides.
journal, February 2006
- Reddy, Chinta Reddy Venkat; Urgaonkar, Sameer; Verkade, John G.
- ChemInform, Vol. 37, Issue 6
Works referencing / citing this record:
Enantiopure encaged Verkade's superbases: Synthesis, chiroptical properties, and use as chiral derivatizing agent
journal, November 2019
- Yang, Jian; Chatelet, Bastien; Hérault, Damien
- Chirality, Vol. 32, Issue 2