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

This content will become publicly available on January 3, 2021

Title: Electroactivated alkylation of amines with alcohols via both direct and indirect borrowing hydrogen mechanisms

Abstract

Aqueous electrocatalytic alkylation of amines with alcohol; water is the only byproduct.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [1];  [1]; ORCiD logo [1]
  1. Dept of Chemistry, Michigan State University, East Lansing, USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1582479
Grant/Contract Number:  
FG36-04GO14216
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Name: Green Chemistry; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Appiagyei, Benjamin, Bhatia, Souful, Keeney, Gabriela L., Dolmetsch, Troy, and Jackson, James E. Electroactivated alkylation of amines with alcohols via both direct and indirect borrowing hydrogen mechanisms. United Kingdom: N. p., 2020. Web. doi:10.1039/C9GC03747K.
Appiagyei, Benjamin, Bhatia, Souful, Keeney, Gabriela L., Dolmetsch, Troy, & Jackson, James E. Electroactivated alkylation of amines with alcohols via both direct and indirect borrowing hydrogen mechanisms. United Kingdom. doi:10.1039/C9GC03747K.
Appiagyei, Benjamin, Bhatia, Souful, Keeney, Gabriela L., Dolmetsch, Troy, and Jackson, James E. Wed . "Electroactivated alkylation of amines with alcohols via both direct and indirect borrowing hydrogen mechanisms". United Kingdom. doi:10.1039/C9GC03747K.
@article{osti_1582479,
title = {Electroactivated alkylation of amines with alcohols via both direct and indirect borrowing hydrogen mechanisms},
author = {Appiagyei, Benjamin and Bhatia, Souful and Keeney, Gabriela L. and Dolmetsch, Troy and Jackson, James E.},
abstractNote = {Aqueous electrocatalytic alkylation of amines with alcohol; water is the only byproduct.},
doi = {10.1039/C9GC03747K},
journal = {Green Chemistry},
number = ,
volume = ,
place = {United Kingdom},
year = {2020},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on January 3, 2021
Publisher's Version of Record

Save / Share:

Works referenced in this record:

Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen
journal, February 1958


The “Borrowing Hydrogen Strategy” by Supported Ruthenium Hydroxide Catalysts: Synthetic Scope of Symmetrically and Unsymmetrically Substituted Amines
journal, May 2010

  • Yamaguchi, Kazuya; He, Jinling; Oishi, Takamichi
  • Chemistry - A European Journal, Vol. 16, Issue 24
  • DOI: 10.1002/chem.201000149

Mild electrocatalytic hydrogenation and hydrodeoxygenation of bio-oil derived phenolic compounds using ruthenium supported on activated carbon cloth
journal, January 2012

  • Li, Zhenglong; Garedew, Mahlet; Lam, Chun Ho
  • Green Chemistry, Vol. 14, Issue 9, p. 2540-2549
  • DOI: 10.1039/c2gc35552c

Model for Aqueous Solvation Based on Class IV Atomic Charges and First Solvation Shell Effects
journal, January 1996

  • Chambers, Candee C.; Hawkins, Gregory D.; Cramer, Christopher J.
  • The Journal of Physical Chemistry, Vol. 100, Issue 40
  • DOI: 10.1021/jp9610776

Gauge-Including Atomic Orbital Proton Chemical Shifts of Strong Hydrogen Bonds:  The Importance of Electron Correlation
journal, May 2001

  • Barich, Dewey H.; Nicholas, John B.; Haw, James F.
  • The Journal of Physical Chemistry A, Vol. 105, Issue 19
  • DOI: 10.1021/jp004118d

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis
journal, January 2018


Heterogeneous catalysis for the direct synthesis of chemicals by borrowing hydrogen methodology
journal, January 2015

  • Shimizu, Ken-ichi
  • Catalysis Science & Technology, Vol. 5, Issue 3
  • DOI: 10.1039/C4CY01170H

Ruthenium-Catalyzed N -Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology
journal, February 2009

  • Hamid, M. Haniti S. A.; Allen, C. Liana; Lamb, Gareth W.
  • Journal of the American Chemical Society, Vol. 131, Issue 5
  • DOI: 10.1021/ja807323a

Palladium catalyzed N-alkylation of amines with alcohols
journal, March 2011


N-Methylation of amines and nitroarenes with methanol using heterogeneous platinum catalysts
journal, March 2019


Stereoretentive C−H Bond Activation in the Aqueous Phase Catalytic Hydrogenation of Amino Acids to Amino Alcohols
journal, February 2003

  • Jere, Frank T.; Miller, Dennis J.; Jackson, James E.
  • Organic Letters, Vol. 5, Issue 4
  • DOI: 10.1021/ol0274211

Selective Synthesis of Secondary Amines via N -Alkylation of Primary Amines and Ammonia with Alcohols by Supported Copper Hydroxide Catalysts
journal, November 2010

  • He, Jinling; Yamaguchi, Kazuya; Mizuno, Noritaka
  • Chemistry Letters, Vol. 39, Issue 11
  • DOI: 10.1246/cl.2010.1182

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions
journal, May 2009

  • Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G.
  • The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396
  • DOI: 10.1021/jp810292n

Ultrastructural Characterization of the Lower Motor System in a Mouse Model of Krabbe Disease
journal, December 2016


Ruthenium-Catalyzed Amination of Secondary Alcohols Using Borrowing Hydrogen Methodology
journal, February 2016


Multialkylation of Aqueous Ammonia with Alcohols Catalyzed by Water-Soluble Cp*Ir−Ammine Complexes
journal, November 2010

  • Kawahara, Ryoko; Fujita, Ken-ichi; Yamaguchi, Ryohei
  • Journal of the American Chemical Society, Vol. 132, Issue 43
  • DOI: 10.1021/ja107274w

Estimation of Absolute Free Energies of Hydration Using Continuum Methods:  Accuracy of Partial Charge Models and Optimization of Nonpolar Contributions
journal, November 2005

  • Rizzo, Robert C.; Aynechi, Tiba; Case, David A.
  • Journal of Chemical Theory and Computation, Vol. 2, Issue 1
  • DOI: 10.1021/ct050097l

Borrowing Hydrogen Methodology for Amine Synthesis under Solvent-Free Microwave Conditions
journal, April 2011

  • Watson, Andrew J. A.; Maxwell, Aoife C.; Williams, Jonathan M. J.
  • The Journal of Organic Chemistry, Vol. 76, Issue 7
  • DOI: 10.1021/jo102521a

Utilization of Common Ligands for the Ruthenium-Catalyzed Amination of Alcohols
journal, November 2013

  • Baumann, Wolfgang; Spannenberg, Anke; Pfeffer, Jan
  • Chemistry - A European Journal, Vol. 19, Issue 52
  • DOI: 10.1002/chem.201302774

Biaryl Phosphane Ligands in Palladium-Catalyzed Amination
journal, August 2008

  • Surry, David S.; Buchwald, Stephen L.
  • Angewandte Chemie International Edition, Vol. 47, Issue 34
  • DOI: 10.1002/anie.200800497

Transition metal-catalysed N-alkylation of amines by alcohols
journal, January 1981

  • Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S.
  • Journal of the Chemical Society, Chemical Communications, Issue 12
  • DOI: 10.1039/c39810000611

Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions
journal, January 1980

  • Krishnan, R.; Binkley, J. S.; Seeger, R.
  • The Journal of Chemical Physics, Vol. 72, Issue 1
  • DOI: 10.1063/1.438955

Ruthenium Complex-Controlled Catalytic N -Mono- or N,N -Dialkylation of Heteroaromatic Amines with Alcohols
journal, January 1996

  • Watanabe, Yoshihisa; Morisaki, Yasuhiro; Kondo, Teruyuki
  • The Journal of Organic Chemistry, Vol. 61, Issue 13
  • DOI: 10.1021/jo9516289

Selective Synthesis of Secondary and Tertiary Amines by Cp*Iridium-Catalyzed Multialkylation of Ammonium Salts with Alcohols
journal, January 2008

  • Yamaguchi, Ryohei; Kawagoe, Shoko; Asai, Chiho
  • Organic Letters, Vol. 10, Issue 2
  • DOI: 10.1021/ol702522k

Stereoselective reductions of substituted cyclohexyl and cyclopentyl carbon-nitrogen .pi. systems with hydride reagents
journal, October 1983

  • Hutchins, Robert O.; Su, Wei Yang; Sivakumar, Ramachandran
  • The Journal of Organic Chemistry, Vol. 48, Issue 20
  • DOI: 10.1021/jo00168a009

Heterogeneously catalyzed selective N-alkylation of aromatic and heteroaromatic amines with alcohols by a supported ruthenium hydroxide
journal, April 2009


Surfactants: Pharmaceutical and Medicinal Aspects [Surfactants: Pharmaceutical and Medicinal Aspects]
journal, May 2013

  • Sekhon, Bhupinder Singh
  • Journal of Pharmaceutical Technology, Research and Management, Vol. 1, Issue 1
  • DOI: 10.15415/jptrm.2013.11004

A comparison of models for calculating nuclear magnetic resonance shielding tensors
journal, April 1996

  • Cheeseman, James R.; Trucks, Gary W.; Keith, Todd A.
  • The Journal of Chemical Physics, Vol. 104, Issue 14
  • DOI: 10.1063/1.471789

Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters: The mPW and mPW1PW models
journal, January 1998

  • Adamo, Carlo; Barone, Vincenzo
  • The Journal of Chemical Physics, Vol. 108, Issue 2
  • DOI: 10.1063/1.475428

N-alkylation of amines with alcohols over alumina-entrapped Ag catalysts using the “borrowing hydrogen” methodology
journal, August 2012


Recent advances in homogeneous borrowing hydrogen catalysis using earth-abundant first row transition metals
journal, January 2019

  • Reed-Berendt, Benjamin G.; Polidano, Kurt; Morrill, Louis C.
  • Organic & Biomolecular Chemistry, Vol. 17, Issue 7
  • DOI: 10.1039/C8OB01895B

Complementation of Biotransformations with Chemical C–H Oxidation: Copper-Catalyzed Oxidation of Tertiary Amines in Complex Pharmaceuticals
journal, August 2013

  • Genovino, Julien; Lütz, Stephan; Sames, Dalibor
  • Journal of the American Chemical Society, Vol. 135, Issue 33
  • DOI: 10.1021/ja405471h

Dissociationsvorgänge bei den einatomigen Alkoholen, Aethern und Salzen
journal, January 1901


Heterogeneous Catalysts for the Guerbet Coupling of Alcohols
journal, June 2013

  • Kozlowski, Joseph T.; Davis, Robert J.
  • ACS Catalysis, Vol. 3, Issue 7
  • DOI: 10.1021/cs400292f

Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
journal, November 1994

  • Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.
  • The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627
  • DOI: 10.1021/j100096a001

Electrocatalysis on Oxide-Stabilized, High-Surface Area Carbon Electrodes
journal, July 2013

  • Méndez, Manuel A.; Alibabaei, Leila; Concepcion, Javier J.
  • ACS Catalysis, Vol. 3, Issue 8
  • DOI: 10.1021/cs4003595

Mechanistic Aspects of C−H Activation by Pt Complexes
journal, June 2005

  • Lersch, Martin; Tilset, Mats
  • Chemical Reviews, Vol. 105, Issue 6
  • DOI: 10.1021/cr030710y

Catalytic Alkylation of Aniline
journal, August 1924

  • Brown, A. B.; Reid, E. Emmet
  • Journal of the American Chemical Society, Vol. 46, Issue 8
  • DOI: 10.1021/ja01673a011

IUPAC-NIST Solubility Data Series. 82. Alcohols with Water—Revised and Updated: Part 1. C4 Alcohols with Water
journal, March 2007

  • Goral, Marian; Wisniewska-Goclowska, Barbara
  • Journal of Physical and Chemical Reference Data, Vol. 36, Issue 1
  • DOI: 10.1063/1.2366707

Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules
journal, March 1972

  • Hehre, W. J.; Ditchfield, R.; Pople, J. A.
  • The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261
  • DOI: 10.1063/1.1677527