Computed thermodynamic stabilities of silylium Lewis base adducts

Roselli, Christina A.; Gagné, Michel R.

doi:10.1039/C8OB00354H

Title: Computed thermodynamic stabilities of silylium Lewis base adducts

Journal Article · Mon Jan 01 00:00:00 EST 2018 · Organic and Biomolecular Chemistry

DOI:https://doi.org/10.1039/C8OB00354H· OSTI ID:1434086

Roselli, Christina A. ^[1];

^[1]

Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, USA

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

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Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-05ER15630

OSTI ID:: 1434086

Journal Information:: Organic and Biomolecular Chemistry, Journal Name: Organic and Biomolecular Chemistry Vol. 16 Journal Issue: 13; ISSN 1477-0520

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 3 works

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References (26)

Silyl Chalconium Ions: Synthesis, Structure and Application in Hydrodefluorination Reactions Kordts, Natalie; Künzler, Sandra; Rathjen, Saskia Chemistry - A European Journal, Vol. 23, Issue 42 https://doi.org/10.1002/chem.201702051	journal	June 2017
Chemoselective Reduction of Tertiary Amides to Amines Catalyzed by Triphenylborane Mukherjee, Debabrata; Shirase, Satoru; Mashima, Kazushi Angewandte Chemie International Edition, Vol. 55, Issue 42 https://doi.org/10.1002/anie.201605236	journal	October 2016
Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis Banik, Steven M.; Levina, Anna; Hyde, Alan M. Science, Vol. 358, Issue 6364 https://doi.org/10.1126/science.aao5894	journal	November 2017
Phosphines as Silylium Ion Carriers for Controlled C–O Deoxygenation: Catalyst Speciation and Turnover Mechanisms Gudz, Anton; Payne, Philippa R.; Gagné, Michel R. Organometallics, Vol. 36, Issue 20 https://doi.org/10.1021/acs.organomet.7b00689	journal	October 2017
Metal-Free Deoxygenation of Carbohydrates Adduci, Laura L.; McLaughlin, Matthew P.; Bender, Trandon A. Angewandte Chemie International Edition, Vol. 53, Issue 6 https://doi.org/10.1002/anie.201306864	journal	January 2014
Reductive Cleavage of Glycosides, Stereochemistry of Trapping of Cyclic Oxonium Ions Rolf, David; Bennek, John A.; Gray, Gary R. Journal of Carbohydrate Chemistry, Vol. 2, Issue 4 https://doi.org/10.1080/07328308308057884	journal	January 1983
Electrophilic Activation of Silicon-Hydrogen Bonds in Catalytic Hydrosilations Lipke, Mark C.; Liberman-Martin, Allegra L.; Tilley, T. Don Angewandte Chemie International Edition, Vol. 56, Issue 9 https://doi.org/10.1002/anie.201605198	journal	January 2017
A Novel B(C ₆ F ₅ ) ₃ -Catalyzed Reduction of Alcohols and Cleavage of Aryl and Alkyl Ethers with Hydrosilanes ^† Gevorgyan, Vladimir; Rubin, Michael; Benson, Sharonda The Journal of Organic Chemistry, Vol. 65, Issue 19 https://doi.org/10.1021/jo000726d	journal	September 2000
B(C ₆ F ₅ ) ₃ -Catalyzed Reduction of Ketones and Imines Using Silicon-Stereogenic Silanes: Stereoinduction by Single-Point Binding Hog, Daniel T.; Oestreich, Martin European Journal of Organic Chemistry, Vol. 2009, Issue 29 https://doi.org/10.1002/ejoc.200900796	journal	October 2009
Late-stage chemoselective functional-group manipulation of bioactive natural products with super-electrophilic silylium ions Bender, Trandon A.; Payne, Philippa R.; Gagné, Michel R. Nature Chemistry, Vol. 10, Issue 1 https://doi.org/10.1038/nchem.2863	journal	September 2017
Diastereoselective B(C ₆ F ₅ ) ₃ -Catalyzed Reductive Carbocyclization of Unsaturated Carbohydrates Bender, Trandon A.; Dabrowski, Jennifer A.; Zhong, Hongyu Organic Letters, Vol. 18, Issue 16 https://doi.org/10.1021/acs.orglett.6b02050	journal	August 2016
Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects Miertuš, S.; Scrocco, E.; Tomasi, J. Chemical Physics, Vol. 55, Issue 1 https://doi.org/10.1016/0301-0104(81)85090-2	journal	February 1981
B(C ₆ F ₅ ) ₃ -Catalyzed Hydrosilation of Imines via Silyliminium Intermediates Blackwell, James M.; Sonmor, Eric R.; Scoccitti, Tiziana Organic Letters, Vol. 2, Issue 24 https://doi.org/10.1021/ol006695q	journal	November 2000
Mechanistic Aspects of Bond Activation with Perfluoroarylboranes Piers, Warren E.; Marwitz, Adam J. V.; Mercier, Lauren G. Inorganic Chemistry, Vol. 50, Issue 24 https://doi.org/10.1021/ic2006474	journal	December 2011
Iridium-Catalyzed Hydrosilylative Reduction of Glucose to Hexane(s) McLaughlin, Matthew P.; Adduci, Laura L.; Becker, Jennifer J. Journal of the American Chemical Society, Vol. 135, Issue 4 https://doi.org/10.1021/ja3110494	journal	January 2013
Establishing the Hydride Donor Abilities of Main Group Hydrides Heiden, Zachariah M.; Lathem, A. Paige Organometallics, Vol. 34, Issue 10 https://doi.org/10.1021/om5011512	journal	May 2015
Silylium ions in catalysis Klare, Hendrik F. T.; Oestreich, Martin Dalton Transactions, Vol. 39, Issue 39 https://doi.org/10.1039/c003097j	journal	January 2010
A unified survey of Si–H and H–H bond activation catalysed by electron-deficient boranes Oestreich, Martin; Hermeke, Julia; Mohr, Jens Chemical Society Reviews, Vol. 44, Issue 8 https://doi.org/10.1039/C4CS00451E	journal	January 2015
Enantioselective Hydrosilylation with Chiral Frustrated Lewis Pairs Chen, Dianjun; Leich, Valeri; Pan, Fangfang Chemistry - A European Journal, Vol. 18, Issue 17 https://doi.org/10.1002/chem.201200244	journal	March 2012
“Tamed” Silylium Ions: Versatile in Catalysis Schulz, Axel; Villinger, Alexander Angewandte Chemie International Edition, Vol. 51, Issue 19 https://doi.org/10.1002/anie.201108320	journal	March 2012
Direct observation of a borane–silane complex involved in frustrated Lewis-pair-mediated hydrosilylations Houghton, Adrian Y.; Hurmalainen, Juha; Mansikkamäki, Akseli Nature Chemistry, Vol. 6, Issue 11 https://doi.org/10.1038/nchem.2063	journal	September 2014
The Silylium Ion Problem, R ₃ Si ⁺ . Bridging Organic and Inorganic Chemistry Reed, Christopher A. Accounts of Chemical Research, Vol. 31, Issue 6 https://doi.org/10.1021/ar960132q	journal	June 1998
Positional Selectivity in the Hydrosilylative Partial Deoxygenation of Disaccharides by Boron Catalysts Seo, Youngran; Gagné, Michel R. ACS Catalysis, Vol. 8, Issue 1 https://doi.org/10.1021/acscatal.7b02992	journal	November 2017
Chemoselective conversion of biologically sourced polyols into chiral synthons Adduci, Laura L.; Bender, Trandon A.; Dabrowski, Jennifer A. Nature Chemistry, Vol. 7, Issue 7 https://doi.org/10.1038/nchem.2277	journal	June 2015
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972

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