Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration
Abstract
Here, this paper reports the first example of dearomatization of ubiquitous terpyridine (tpy) ligands via 2'/6'-, 3'/5'-, or 4'-selective alkylation of the central pyridine ring. The reaction is mediated by the most abundant metal in the Earth’s crust, aluminum (Al), and depending on the conditions employed, exhibits ionic or radical character as suggested by experimental and computational analysis. In the latter case, intermediate formation of an AlIII complex supported by π-radical monoanionic ligand (tpy•)1– is apparent. The 3'/5'-alkylation leads to unprecedented zwitterionic Meisenheimer AlIII complexes, which were identified as efficient precatalysts for the selective hydroboration of C=O and C≡C functionalities. Turnover numbers (TONs) up to ~1000 place the corresponding complexes in the category of the most efficient Al catalysts reported to date for the title reaction. The acquired data suggest that aluminum monohydrides, or more likely dihydrides, could be relevant catalytic species. Alternatively, one can also imagine a mechanistic scenario in which the dearomatized “chemically noninnocent” ligand acts as hydride donor, and a detailed investigation of this is warranted in the future.
- Authors:
-
- City Univ. (CUNY), NY (United States). Graduate Center, Dept. of Sciences, John Jay College
- City Univ. (CUNY), NY (United States). Graduate Center, Dept. of Sciences, John Jay College; City Univ. (CUNY), NY (United States). Hunter College, Dept. of Chemistry
- City Univ. (CUNY), NY (United States). Hunter College, Dept. of Chemistry
- Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
- Publication Date:
- Research Org.:
- Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
- Sponsoring Org.:
- National Science Foundation (NSF); John Jay College; USDOE
- OSTI Identifier:
- 1492666
- Report Number(s):
- LA-UR-18-24664
Journal ID: ISSN 2155-5435
- Grant/Contract Number:
- 89233218CNA000001
- Resource Type:
- Journal Article: Accepted Manuscript
- Journal Name:
- ACS Catalysis
- Additional Journal Information:
- Journal Volume: 9; Journal ID: ISSN 2155-5435
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Inorganic and Physical Chemistry; Organic Chemistry
Citation Formats
Zhang, Guoqi, Wu, Jing, Zeng, Haisu, Neary, Michelle C., Devany, Matthew, Zheng, Shengping, and Dub, Pavel A. Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration. United States: N. p., 2018.
Web. doi:10.1021/acscatal.8b04096.
Zhang, Guoqi, Wu, Jing, Zeng, Haisu, Neary, Michelle C., Devany, Matthew, Zheng, Shengping, & Dub, Pavel A. Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration. United States. https://doi.org/10.1021/acscatal.8b04096
Zhang, Guoqi, Wu, Jing, Zeng, Haisu, Neary, Michelle C., Devany, Matthew, Zheng, Shengping, and Dub, Pavel A. 2018.
"Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration". United States. https://doi.org/10.1021/acscatal.8b04096. https://www.osti.gov/servlets/purl/1492666.
@article{osti_1492666,
title = {Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration},
author = {Zhang, Guoqi and Wu, Jing and Zeng, Haisu and Neary, Michelle C. and Devany, Matthew and Zheng, Shengping and Dub, Pavel A.},
abstractNote = {Here, this paper reports the first example of dearomatization of ubiquitous terpyridine (tpy) ligands via 2'/6'-, 3'/5'-, or 4'-selective alkylation of the central pyridine ring. The reaction is mediated by the most abundant metal in the Earth’s crust, aluminum (Al), and depending on the conditions employed, exhibits ionic or radical character as suggested by experimental and computational analysis. In the latter case, intermediate formation of an AlIII complex supported by π-radical monoanionic ligand (tpy•)1– is apparent. The 3'/5'-alkylation leads to unprecedented zwitterionic Meisenheimer AlIII complexes, which were identified as efficient precatalysts for the selective hydroboration of C=O and C≡C functionalities. Turnover numbers (TONs) up to ~1000 place the corresponding complexes in the category of the most efficient Al catalysts reported to date for the title reaction. The acquired data suggest that aluminum monohydrides, or more likely dihydrides, could be relevant catalytic species. Alternatively, one can also imagine a mechanistic scenario in which the dearomatized “chemically noninnocent” ligand acts as hydride donor, and a detailed investigation of this is warranted in the future.},
doi = {10.1021/acscatal.8b04096},
url = {https://www.osti.gov/biblio/1492666},
journal = {ACS Catalysis},
issn = {2155-5435},
number = ,
volume = 9,
place = {United States},
year = {Mon Dec 31 00:00:00 EST 2018},
month = {Mon Dec 31 00:00:00 EST 2018}
}
Web of Science
Works referenced in this record:
The role of the metal-bound N–H functionality in Noyori-type molecular catalysts
journal, November 2018
- Dub, Pavel A.; Gordon, John C.
- Nature Reviews Chemistry, Vol. 2, Issue 12
Metal–Ligand Bifunctional Catalysis: The “Accepted” Mechanism, the Issue of Concertedness, and the Function of the Ligand in Catalytic Cycles Involving Hydrogen Atoms
journal, September 2017
- Dub, Pavel A.; Gordon, John C.
- ACS Catalysis, Vol. 7, Issue 10
Non-innocent ligands
journal, January 2015
- Berben, Louise A.; de Bruin, Bas; Heyduk, Alan F.
- Chemical Communications, Vol. 51, Issue 9
Redox Non-Innocent Ligands: Versatile New Tools to Control Catalytic Reactions
journal, January 2012
- Lyaskovskyy, Volodymyr; de Bruin, Bas
- ACS Catalysis, Vol. 2, Issue 2
Systematics and Future Projections Concerning Redox-Noninnocent Amide/Imine Ligands
journal, November 2011
- Caulton, Kenneth G.
- European Journal of Inorganic Chemistry, Vol. 2012, Issue 3
Preface: Forum on Redox-Active Ligands
journal, October 2011
- Chirik, Paul J.
- Inorganic Chemistry, Vol. 50, Issue 20
Radical Ligands Confer Nobility on Base-Metal Catalysts
journal, February 2010
- Chirik, P. J.; Wieghardt, K.
- Science, Vol. 327, Issue 5967
Metal complexes with non-innocent ligands
journal, June 2005
- Butin, Kim P.; Beloglazkina, Elena K.; Zyk, Nikolai V.
- Russian Chemical Reviews, Vol. 74, Issue 6
The synthesis of 2,2′:6′,2″-terpyridine ligands — versatile building blocks for supramolecular chemistry
journal, April 1997
- Cargill Thompson, Alexander M. W.
- Coordination Chemistry Reviews, Vol. 160
Evidence for a Ni I Active Species in the Catalytic Cross-Coupling of Alkyl Electrophiles
journal, July 2004
- Anderson, Thomas J.; Jones, Gavin D.; Vicic, David A.
- Journal of the American Chemical Society, Vol. 126, Issue 26
Ligand Redox Effects in the Synthesis, Electronic Structure, and Reactivity of an Alkyl−Alkyl Cross-Coupling Catalyst
journal, October 2006
- Jones, Gavin D.; Martin, Jason L.; McFarland, Chris
- Journal of the American Chemical Society, Vol. 128, Issue 40
High-Activity Cobalt Catalysts for Alkene Hydroboration with Electronically Responsive Terpyridine and α-Diimine Ligands
journal, December 2014
- Palmer, W. Neil; Diao, Tianning; Pappas, Iraklis
- ACS Catalysis, Vol. 5, Issue 2
Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction
journal, May 2018
- Friedfeld, Max R.; Zhong, Hongyu; Ruck, Rebecca T.
- Science, Vol. 360, Issue 6391
Reaction: Earth-Abundant Metal Catalysts for Energy Conversions
journal, April 2017
- Bullock, R. Morris
- Chem, Vol. 2, Issue 4
Hydrogenation of carboxylic acids with a homogeneous cobalt catalyst
journal, October 2015
- Korstanje, T. J.; Ivar van der Vlugt, J.; Elsevier, C. J.
- Science, Vol. 350, Issue 6258
Abundant Metals Give Precious Hydrogenation Performance
journal, November 2013
- Bullock, R. M.
- Science, Vol. 342, Issue 6162
Amine(imine)diphosphine Iron Catalysts for Asymmetric Transfer Hydrogenation of Ketones and Imines
journal, November 2013
- Zuo, W.; Lough, A. J.; Li, Y. F.
- Science, Vol. 342, Issue 6162
Cobalt Precursors for High-Throughput Discovery of Base Metal Asymmetric Alkene Hydrogenation Catalysts
journal, November 2013
- Friedfeld, M. R.; Shevlin, M.; Hoyt, J. M.
- Science, Vol. 342, Issue 6162
Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines
journal, November 2013
- Jagadeesh, R. V.; Surkus, A. -E.; Junge, H.
- Science, Vol. 342, Issue 6162
A Pharmaceutical Industry Perspective on Sustainable Metal Catalysis
journal, October 2018
- Hayler, John D.; Leahy, David K.; Simmons, Eric M.
- Organometallics, Vol. 38, Issue 1
From Ruthenium to Iron and Manganese-A Mechanistic View on Challenges and Design Principles of Base-Metal Hydrogenation Catalysts
journal, March 2018
- Zell, Thomas; Langer, Robert
- ChemCatChem, Vol. 10, Issue 9
Catalytic (de)hydrogenation promoted by non-precious metals – Co, Fe and Mn: recent advances in an emerging field
journal, January 2018
- Filonenko, Georgy A.; van Putten, Robbert; Hensen, Emiel J. M.
- Chemical Society Reviews, Vol. 47, Issue 4
Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis
journal, May 2017
- Zweig, Joshua E.; Kim, Daria E.; Newhouse, Timothy R.
- Chemical Reviews, Vol. 117, Issue 18
Iron Group Hydrides in Noyori Bifunctional Catalysis
journal, August 2016
- Morris, Robert H.
- The Chemical Record, Vol. 16, Issue 6
Cooperative Catalysis with First-Row Late Transition Metals
journal, September 2011
- van der Vlugt, Jarl Ivar; de Bruin, Bas
- European Journal of Inorganic Chemistry, Vol. 2012, Issue 3, p. 363-375
Getting Down to Earth: The Renaissance of Catalysis with Abundant Metals
journal, August 2015
- Chirik, Paul; Morris, Robert
- Accounts of Chemical Research, Vol. 48, Issue 9
New Tricks for an Old Dog: Aluminum Compounds as Catalysts in Reduction Chemistry
journal, September 2017
- Nikonov, Georgii I.
- ACS Catalysis, Vol. 7, Issue 10
Soluble aluminum hydrides function as catalysts in deprotonation, insertion, and activation reactions
journal, November 2017
- Li, Wenling; Ma, Xiaoli; Walawalkar, Mrinalini G.
- Coordination Chemistry Reviews, Vol. 350
The Renaissance of Aluminum Chemistry †
journal, November 2004
- Roesky, Herbert W.
- Inorganic Chemistry, Vol. 43, Issue 23
Aluminum-Catalyzed Hydroboration of Alkenes
journal, January 2018
- Bismuto, Alessandro; Cowley, Michael J.; Thomas, Stephen P.
- ACS Catalysis, Vol. 8, Issue 3
Comparing Neutral (Monometallic) and Anionic (Bimetallic) Aluminum Complexes in Hydroboration Catalysis: Influences of Lithium Cooperation and Ligand Set
journal, August 2018
- Pollard, Victoria A.; Fuentes, M. Ángeles; Kennedy, Alan R.
- Angewandte Chemie International Edition, Vol. 57, Issue 33
Lithium diamidodihydridoaluminates: bimetallic cooperativity in catalytic hydroboration and metallation applications
journal, January 2018
- Pollard, Victoria A.; Orr, Samantha A.; McLellan, Ross
- Chemical Communications, Vol. 54, Issue 10
An Aluminum Dihydride Working as a Catalyst in Hydroboration and Dehydrocoupling
journal, February 2016
- Yang, Zhi; Zhong, Mingdong; Ma, Xiaoli
- Journal of the American Chemical Society, Vol. 138, Issue 8
Aluminum Hydride Catalyzed Hydroboration of Alkynes
journal, November 2016
- Bismuto, Alessandro; Thomas, Stephen P.; Cowley, Michael J.
- Angewandte Chemie International Edition, Vol. 55, Issue 49
Aluminum Hydrides Stabilized by N-Heterocyclic Imines as Catalysts for Hydroborations with Pinacolborane: Aluminum Hydrides Stabilized by N-Heterocyclic Imines as Catalysts for Hydroborations with Pinacolborane
journal, November 2016
- Franz, Daniel; Sirtl, Lorenz; Pöthig, Alexander
- Zeitschrift für anorganische und allgemeine Chemie, Vol. 642, Issue 22
An Aluminum Hydride That Functions like a Transition-Metal Catalyst
journal, June 2015
- Yang, Zhi; Zhong, Mingdong; Ma, Xiaoli
- Angewandte Chemie International Edition, Vol. 54, Issue 35
Aluminum–Ligand Cooperative N–H Bond Activation and an Example of Dehydrogenative Coupling
journal, June 2013
- Myers, Thomas W.; Berben, Louise A.
- Journal of the American Chemical Society, Vol. 135, Issue 27
A Powerful Aluminum Catalyst for the Synthesis of Highly Functional Organic Carbonates
journal, January 2013
- Whiteoak, Christopher J.; Kielland, Nicola; Laserna, Victor
- Journal of the American Chemical Society, Vol. 135, Issue 4
Catalysis by Aluminum(III) Complexes of Non-Innocent Ligands
journal, November 2014
- Berben, Louise A.
- Chemistry - A European Journal, Vol. 21, Issue 7
Interconversion of Molybdenum Imido and Amido Complexes by Proton-Coupled Electron Transfer
journal, January 2018
- Bezdek, Máté J.; Chirik, Paul J.
- Angewandte Chemie International Edition, Vol. 57, Issue 8
Highly Selective Hydroboration of Alkenes, Ketones and Aldehydes Catalyzed by a Well-Defined Manganese Complex
journal, October 2016
- Zhang, Guoqi; Zeng, Haisu; Wu, Jing
- Angewandte Chemie International Edition, Vol. 55, Issue 46
Dearomatization and Functionalization of Terpyridine by Lutetium(III) Alkyl Complexes
journal, April 2006
- Jantunen, Kimberly C.; Scott, Brian L.; Hay, P. Jeffrey
- Journal of the American Chemical Society, Vol. 128, Issue 19
Reaction of the Diimine Pyridine Ligand with Aluminum Alkyls: An Unexpectedly Complex Reaction
journal, February 2006
- Knijnenburg, Quinten; Smits, Jan M. M.; Budzelaar, Peter H. M.
- Organometallics, Vol. 25, Issue 4
Ligand-centred reactivity in diiminepyridine complexes
journal, January 2006
- Knijnenburg, Quinten; Gambarotta, Sandro; Budzelaar, Peter H. M.
- Dalton Transactions, Issue 46
Life and Death of an Active Ethylene Polymerization Catalyst. Ligand Involvement in Catalyst Activation and Deactivation. Isolation and Characterization of Two Unprecedented Neutral and Anionic Vanadium(I) Alkyls
journal, October 1999
- Reardon, Damien; Conan, Françoise; Gambarotta, Sandro
- Journal of the American Chemical Society, Vol. 121, Issue 40
Some aspects of anionic .sigma.-complexes
journal, August 1982
- Artamkina, G. A.; Egorov, M. P.; Beletskaya, I. P.
- Chemical Reviews, Vol. 82, Issue 4
Radical Chemistry of Iminepyridine Ligands
journal, September 2011
- Budzelaar, Peter H. M.
- European Journal of Inorganic Chemistry, Vol. 2012, Issue 3
Mechanism of Alkyl Migration in Diorganomagnesium 2,6-Bis(imino)pyridine Complexes: Formation of Grignard-Type Complexes with Square-Planar Mg(II) Centers
journal, September 2016
- Sandoval, John J.; Palma, Pilar; Álvarez, Eleuterio
- Organometallics, Vol. 35, Issue 18
Performance of Density Functional Theory for Second Row (4 d ) Transition Metal Thermochemistry
journal, August 2013
- Laury, Marie L.; Wilson, Angela K.
- Journal of Chemical Theory and Computation, Vol. 9, Issue 9
Catalytic Hydroboration of Carbonyl Derivatives, Imines, and Carbon Dioxide
journal, April 2015
- Chong, Che Chang; Kinjo, Rei
- ACS Catalysis, Vol. 5, Issue 6
Selection of boron reagents for Suzuki–Miyaura coupling
journal, January 2014
- Lennox, Alastair J. J.; Lloyd-Jones, Guy C.
- Chem. Soc. Rev., Vol. 43, Issue 1
Recent developments in alkyne borylations
journal, November 2014
- Barbeyron, Renaud; Benedetti, Erica; Cossy, Janine
- Tetrahedron, Vol. 70, Issue 45
Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin
journal, January 2005
- Trost, Barry M.; Ball, Zachary T.
- Synthesis, Vol. 2005, Issue 06
Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds
journal, August 2016
- Jakhar, Vineet Kumar; Barman, Milan Kr.; Nembenna, Sharanappa
- Organic Letters, Vol. 18, Issue 18
“Turning Over” Definitions in Catalytic Cycles
journal, November 2012
- Kozuch, Sebastian; Martin, Jan M. L.
- ACS Catalysis, Vol. 2, Issue 12
Alkali Metal Hydridotriphenylborates [(L)M][HBPh 3 ] (M = Li, Na, K): Chemoselective Catalysts for Carbonyl and CO 2 Hydroboration
journal, August 2016
- Mukherjee, Debabrata; Osseili, Hassan; Spaniol, Thomas P.
- Journal of the American Chemical Society, Vol. 138, Issue 34
Magnesium hydridotriphenylborate [Mg(thf) 6 ][HBPh 3 ] 2 : a versatile hydroboration catalyst
journal, January 2016
- Mukherjee, Debabrata; Shirase, Satoru; Spaniol, Thomas P.
- Chemical Communications, Vol. 52, Issue 89
Low Coordinate Germanium(II) and Tin(II) Hydride Complexes: Efficient Catalysts for the Hydroboration of Carbonyl Compounds
journal, February 2014
- Hadlington, Terrance J.; Hermann, Markus; Frenking, Gernot
- Journal of the American Chemical Society, Vol. 136, Issue 8
Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst
journal, January 2017
- Weidner, Victoria L.; Barger, Christopher J.; Delferro, Massimiliano
- ACS Catalysis, Vol. 7, Issue 2
Extremely efficient hydroboration of ketones and aldehydes by copper carbene catalysis
journal, January 2016
- Bagherzadeh, Sharareh; Mankad, Neal P.
- Chemical Communications, Vol. 52, Issue 19
Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines
journal, March 2016
- King, Amanda E.; Stieber, S. Chantal E.; Henson, Neil J.
- European Journal of Inorganic Chemistry, Vol. 2016, Issue 11
Activation and discovery of earth-abundant metal catalysts using sodium tert-butoxide
journal, January 2017
- Docherty, Jamie H.; Peng, Jingying; Dominey, Andrew P.
- Nature Chemistry, Vol. 9, Issue 6
Catalytic hydroboration of aldehydes, ketones, alkynes and alkenes initiated by NaOH
journal, January 2017
- Wu, Yile; Shan, Changkai; Ying, Jianxi
- Green Chemistry, Vol. 19, Issue 17
Straightforward Iron-Catalyzed Synthesis of Vinylboronates by the Hydroboration of Alkynes
journal, November 2012
- Haberberger, Michael; Enthaler, Stephan
- Chemistry - An Asian Journal, Vol. 8, Issue 1
Hydroboration of Alkynes Catalyzed by Pyrrolide-Based PNP Pincer–Iron Complexes
journal, July 2017
- Nakajima, Kazunari; Kato, Takeru; Nishibayashi, Yoshiaki
- Organic Letters, Vol. 19, Issue 16
(CAAC)CuX-catalyzed hydroboration of terminal alkynes with pinacolborane directed by the X-ligand
journal, February 2017
- Romero, Erik A.; Jazzar, Rodolphe; Bertrand, Guy
- Journal of Organometallic Chemistry, Vol. 829
Hydroboration of alkynes and nitriles using an α-diimine cobalt hydride catalyst
journal, January 2017
- Ben-Daat, Hagit; Rock, Christopher L.; Flores, Marco
- Chemical Communications, Vol. 53, Issue 53
σ-Bond Metathesis: A 30-Year Retrospective
journal, September 2013
- Waterman, Rory
- Organometallics, Vol. 32, Issue 24
Iron-Catalyzed Hydroboration: Unlocking Reactivity through Ligand Modulation
journal, July 2016
- Espinal-Viguri, Maialen; Woof, Callum R.; Webster, Ruth L.
- Chemistry - A European Journal, Vol. 22, Issue 33
Intrinsic reaction coordinate: Calculation, bifurcation, and automated search
journal, September 2014
- Maeda, Satoshi; Harabuchi, Yu; Ono, Yuriko
- International Journal of Quantum Chemistry, Vol. 115, Issue 5
The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts
journal, January 2016
- Dub, Pavel A.; Gordon, John C.
- Dalton Transactions, Vol. 45, Issue 16
Outer sphere hydrogenation catalysis
journal, January 2013
- Eisenstein, Odile; Crabtree, Robert H.
- New J. Chem., Vol. 37, Issue 1
Neutral Bis(imino)-1,4-dihydropyridinate and Cationic Bis(imino)pyridine σ-Alkylzinc(II) Complexes as Hydride Exchange Systems: Classic Organometallic Chemistry Meets Ligand-Centered, Biomimetic Reactivity
journal, May 2018
- Sandoval, John J.; Álvarez, Eleuterio; Palma, Pilar
- Organometallics, Vol. 37, Issue 11
(Amidomethyl)pyridine zirconium and hafnium complexes: Synthesis and structural characterization
journal, April 2008
- Nienkemper, Katrin; Kehr, Gerald; Kehr, Seda
- Journal of Organometallic Chemistry, Vol. 693, Issue 8-9
Zinc Complexes with the Chelating Amido-Imino Ligand [1-n-Butyl-2-(2,6-diisopropylphenyl)iminoacenaphthen-1-yl]-2,6-diisopropylphenylamide (L): Synthesis, Molecular Structure and Reactivity of [(L)ZnCl]2, (L)Zn-nBu and (L)ZnN(SiMe3)2
journal, January 2008
- Fedushkin, Igor L.; Tishkina, Alexandra N.; Fukin, Georgii K.
- European Journal of Inorganic Chemistry, Vol. 2008, Issue 3
Selective Alkylation of 2,6-Diiminopyridine Ligands by Dialkylmanganese Reagents: A “One-Pot” Synthetic Methodology
journal, February 2007
- Cámpora, Juan; Pérez, Carmen M.; Rodríguez-Delgado, Antonio
- Organometallics, Vol. 26, Issue 4
Complexation of dimethylmagnesium with α-diimines; structural and EPR characterisation of single electron and alkyl transfer products
journal, January 2006
- Bailey, Philip J.; Dick, Caroline M.; Fabre, Sylvie
- Dalton Transactions, Issue 13
Reaction of â[MnII(CH2tBu)2]â with Bidentate Diimine Ligands: From Simple Base Adducts to CbC Activation of the Ligand We are indebted to the CNRS and ESCPE Lyon for financial support. V.R. is grateful to the Région Rhône-Alpes for a predoctoral fellowship. We also thank Prof. R. A. Andersen (U. C. Berkeley), Prof. Dr. Koelher (TUM), Dr. R. Gauvin (LCOMS), and Dr. C. Boisson (LCPP) for helpful discussions.
journal, August 2002
- Riollet, Virginie; Copéret, Christophe; Basset, Jean-Marie
- Angewandte Chemie International Edition, Vol. 41, Issue 16
Synthesis and structural characterisation of aluminium imino-amide and pyridyl-amide complexes: bulky monoanionic N,N chelate ligands via methyl group transfer1Dedicated to Professor Ken Wade on the occasion of his 65th birthday in recognition of his outstanding contributions to inorganic chemistry.1
journal, January 1998
- Gibson, Vernon C.; Redshaw, Carl; White, Andrew J. P.
- Journal of Organometallic Chemistry, Vol. 550, Issue 1-2
Alkylation Reactions of Dialkylzinc Compounds with 1,4-Diaza-1,3-butadienes: Cationic and Radical Anionic Organozinc Intermediates. Molecular Structure of the Cationic Organozinc Species [MeZn(tert-BuN:CHCH:N-tert-Bu)]O3SCF3 and Me2Zn(bpy) (bpy = 2,2'-Bipyridine)
journal, June 1994
- Wissing, Elmo; Kaupp, Martin; Boersma, Jaap
- Organometallics, Vol. 13, Issue 6
Organozinc .alpha.-Diimine Radicals, Synthesis and Reactivity toward Alkyl Halides
journal, July 1994
- Wissing, Elmo; van der Linden, Steven; Rijnberg, Evelien
- Organometallics, Vol. 13, Issue 7
Stable 1,4-diaza-1,3-butadiene(α-diimine)-zinc and -aluminium radicals formed in single electron transfer reactions: their consequences for organic syntheses
journal, July 1983
- Van Koten, Gerard; Jastrzebski, Johann T. B. H.; Vrieze, Kees
- Journal of Organometallic Chemistry, Vol. 250, Issue 1
Works referencing / citing this record:
Lithium triethylborohydride as catalyst for solvent-free hydroboration of aldehydes and ketones
journal, January 2019
- Kuciński, Krzysztof; Hreczycho, Grzegorz
- Green Chemistry, Vol. 21, Issue 8
1-D manganese( ii )-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds
journal, January 2020
- Zhang, Guoqi; Zeng, Haisu; Li, Sihan
- Dalton Transactions, Vol. 49, Issue 8
Rh( iii )-Catalyzed switchable C–H functionalization of 2-(1 H -pyrazol-1-yl)pyridine with internal alkynes
journal, January 2020
- Wu, Shaonan; Wang, Zhuo; Ma, Dianxue
- Organic Chemistry Frontiers, Vol. 7, Issue 9
Highly efficient and selective hydroboration of terminal and internal alkynes catalysed by a cobalt( ii ) coordination polymer
journal, January 2019
- Zhang, Guoqi; Li, Sihan; Wu, Jing
- Organic Chemistry Frontiers, Vol. 6, Issue 18
n BuLi-promoted anti -Markovnikov selective hydroboration of unactivated alkenes and internal alkynes
journal, January 2019
- Wang, Zi-Chao; Wang, Min; Gao, Jian
- Organic Chemistry Frontiers, Vol. 6, Issue 16
Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters
journal, January 2019
- Wang, Zi-Chao; Shen, Di; Gao, Jian
- Chemical Communications, Vol. 55, Issue 60
Catalyst-Free Approach for Hydroboration of Carboxylic Acids under Mild Conditions
journal, April 2019
- Xu, Xiaojuan; Yan, Dandan; Zhu, Zhangye
- ACS Omega, Vol. 4, Issue 4