DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Computed thermodynamic stabilities of silylium Lewis base adducts

Abstract

We report a computational study of the transfer of silylium from phosphine to heteroatom containing Lewis bases including ethers, phosphines, and amines.

Authors:
 [1]; ORCiD logo [1]
  1. Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1434086
Grant/Contract Number:  
FG02-05ER15630
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Organic and Biomolecular Chemistry
Additional Journal Information:
Journal Name: Organic and Biomolecular Chemistry Journal Volume: 16 Journal Issue: 13; Journal ID: ISSN 1477-0520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Roselli, Christina A., and Gagné, Michel R. Computed thermodynamic stabilities of silylium Lewis base adducts. United Kingdom: N. p., 2018. Web. doi:10.1039/C8OB00354H.
Roselli, Christina A., & Gagné, Michel R. Computed thermodynamic stabilities of silylium Lewis base adducts. United Kingdom. https://doi.org/10.1039/C8OB00354H
Roselli, Christina A., and Gagné, Michel R. Mon . "Computed thermodynamic stabilities of silylium Lewis base adducts". United Kingdom. https://doi.org/10.1039/C8OB00354H.
@article{osti_1434086,
title = {Computed thermodynamic stabilities of silylium Lewis base adducts},
author = {Roselli, Christina A. and Gagné, Michel R.},
abstractNote = {We report a computational study of the transfer of silylium from phosphine to heteroatom containing Lewis bases including ethers, phosphines, and amines.},
doi = {10.1039/C8OB00354H},
journal = {Organic and Biomolecular Chemistry},
number = 13,
volume = 16,
place = {United Kingdom},
year = {Mon Jan 01 00:00:00 EST 2018},
month = {Mon Jan 01 00:00:00 EST 2018}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C8OB00354H

Citation Metrics:
Cited by: 3 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Silyl Chalconium Ions: Synthesis, Structure and Application in Hydrodefluorination Reactions
journal, June 2017

  • Kordts, Natalie; Künzler, Sandra; Rathjen, Saskia
  • Chemistry - A European Journal, Vol. 23, Issue 42
  • DOI: 10.1002/chem.201702051

Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane
journal, October 2016

  • Mukherjee, Debabrata; Shirase, Satoru; Mashima, Kazushi
  • Angewandte Chemie International Edition, Vol. 55, Issue 42
  • DOI: 10.1002/anie.201605236

Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis
journal, November 2017


Phosphines as Silylium Ion Carriers for Controlled C–O Deoxygenation: Catalyst Speciation and Turnover Mechanisms
journal, October 2017


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

Reductive Cleavage of Glycosides, Stereochemistry of Trapping of Cyclic Oxonium Ions
journal, January 1983

  • Rolf, David; Bennek, John A.; Gray, Gary R.
  • Journal of Carbohydrate Chemistry, Vol. 2, Issue 4
  • DOI: 10.1080/07328308308057884

Electrophilic Activation of Silicon-Hydrogen Bonds in Catalytic Hydrosilations
journal, January 2017

  • Lipke, Mark C.; Liberman-Martin, Allegra L.; Tilley, T. Don
  • Angewandte Chemie International Edition, Vol. 56, Issue 9
  • DOI: 10.1002/anie.201605198

A Novel B(C 6 F 5 ) 3 -Catalyzed Reduction of Alcohols and Cleavage of Aryl and Alkyl Ethers with Hydrosilanes
journal, September 2000

  • Gevorgyan, Vladimir; Rubin, Michael; Benson, Sharonda
  • The Journal of Organic Chemistry, Vol. 65, Issue 19
  • DOI: 10.1021/jo000726d

B(C 6 F 5 ) 3 -Catalyzed Reduction of Ketones and Imines Using Silicon-Stereogenic Silanes: Stereoinduction by Single-Point Binding
journal, October 2009

  • Hog, Daniel T.; Oestreich, Martin
  • European Journal of Organic Chemistry, Vol. 2009, Issue 29
  • DOI: 10.1002/ejoc.200900796

Late-stage chemoselective functional-group manipulation of bioactive natural products with super-electrophilic silylium ions
journal, September 2017

  • Bender, Trandon A.; Payne, Philippa R.; Gagné, Michel R.
  • Nature Chemistry, Vol. 10, Issue 1
  • DOI: 10.1038/nchem.2863

Diastereoselective B(C 6 F 5 ) 3 -Catalyzed Reductive Carbocyclization of Unsaturated Carbohydrates
journal, August 2016


B(C 6 F 5 ) 3 -Catalyzed Hydrosilation of Imines via Silyliminium Intermediates
journal, November 2000

  • Blackwell, James M.; Sonmor, Eric R.; Scoccitti, Tiziana
  • Organic Letters, Vol. 2, Issue 24
  • DOI: 10.1021/ol006695q

Mechanistic Aspects of Bond Activation with Perfluoroarylboranes
journal, December 2011

  • Piers, Warren E.; Marwitz, Adam J. V.; Mercier, Lauren G.
  • Inorganic Chemistry, Vol. 50, Issue 24
  • DOI: 10.1021/ic2006474

Iridium-Catalyzed Hydrosilylative Reduction of Glucose to Hexane(s)
journal, January 2013

  • McLaughlin, Matthew P.; Adduci, Laura L.; Becker, Jennifer J.
  • Journal of the American Chemical Society, Vol. 135, Issue 4
  • DOI: 10.1021/ja3110494

Establishing the Hydride Donor Abilities of Main Group Hydrides
journal, May 2015

  • Heiden, Zachariah M.; Lathem, A. Paige
  • Organometallics, Vol. 34, Issue 10
  • DOI: 10.1021/om5011512

Silylium ions in catalysis
journal, January 2010

  • Klare, Hendrik F. T.; Oestreich, Martin
  • Dalton Transactions, Vol. 39, Issue 39
  • DOI: 10.1039/c003097j

A unified survey of Si–H and H–H bond activation catalysed by electron-deficient boranes
journal, January 2015

  • Oestreich, Martin; Hermeke, Julia; Mohr, Jens
  • Chemical Society Reviews, Vol. 44, Issue 8
  • DOI: 10.1039/C4CS00451E

Enantioselective Hydrosilylation with Chiral Frustrated Lewis Pairs
journal, March 2012

  • Chen, Dianjun; Leich, Valeri; Pan, Fangfang
  • Chemistry - A European Journal, Vol. 18, Issue 17
  • DOI: 10.1002/chem.201200244

“Tamed” Silylium Ions: Versatile in Catalysis
journal, March 2012

  • Schulz, Axel; Villinger, Alexander
  • Angewandte Chemie International Edition, Vol. 51, Issue 19
  • DOI: 10.1002/anie.201108320

Direct observation of a borane–silane complex involved in frustrated Lewis-pair-mediated hydrosilylations
journal, September 2014

  • Houghton, Adrian Y.; Hurmalainen, Juha; Mansikkamäki, Akseli
  • Nature Chemistry, Vol. 6, Issue 11
  • DOI: 10.1038/nchem.2063

The Silylium Ion Problem, R 3 Si + . Bridging Organic and Inorganic Chemistry
journal, June 1998

  • Reed, Christopher A.
  • Accounts of Chemical Research, Vol. 31, Issue 6
  • DOI: 10.1021/ar960132q

Positional Selectivity in the Hydrosilylative Partial Deoxygenation of Disaccharides by Boron Catalysts
journal, November 2017


Chemoselective conversion of biologically sourced polyols into chiral synthons
journal, June 2015

  • Adduci, Laura L.; Bender, Trandon A.; Dabrowski, Jennifer A.
  • Nature Chemistry, Vol. 7, Issue 7
  • DOI: 10.1038/nchem.2277

Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections
journal, January 2008

  • Chai, Jeng-Da; Head-Gordon, Martin
  • Physical Chemistry Chemical Physics, Vol. 10, Issue 44
  • DOI: 10.1039/b810189b

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