Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage

Patnaik, Smita; Sadow, Aaron D.

doi:10.1002/ange.201813305

Title: Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage

Abstract

Abstract The high catalytic reactivity of homoleptic tris(alkyl) lanthanum La{C(SiHMe ₂ ) ₃ } ₃ is highlighted by C−O bond cleavage in the hydroboration of esters and epoxides at room temperature. The catalytic hydroboration tolerates functionality typically susceptible to insertion, reduction, or cleavage reactions. Turnover numbers (TON) up to 10 000 are observed for aliphatic esters. Lanthanum hydrides, generated by reactions with pinacolborane, are competent for reduction of ketones but are inert toward esters. Instead, catalytic reduction of esters requires activation of the lanthanum hydride by pinacolborane.

Authors:

Patnaik, Smita ^[1];

^[1]

Department of Chemistry and US Department of Energy Ames Laboratory Iowa State University 1605 Gilman Hall Ames IA USA

Publication Date:: Fri Jan 25 00:00:00 EST 2019

Sponsoring Org.:: USDOE

OSTI Identifier:: 1492099

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie

Additional Journal Information:: Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 8; Journal ID: ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Patnaik, Smita, and Sadow, Aaron D. Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage.  Germany: N. p., 2019. 
Web.  doi:10.1002/ange.201813305.

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                    Patnaik, Smita, & Sadow, Aaron D. Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage.  Germany.  https://doi.org/10.1002/ange.201813305

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                    Patnaik, Smita, and Sadow, Aaron D. Fri .  
"Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage".  Germany.  https://doi.org/10.1002/ange.201813305.

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@article{osti_1492099,

  title        = {Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage},

  author       = {Patnaik, Smita and Sadow, Aaron D.},

  abstractNote = {Abstract The high catalytic reactivity of homoleptic tris(alkyl) lanthanum La{C(SiHMe 2 ) 3 } 3 is highlighted by C−O bond cleavage in the hydroboration of esters and epoxides at room temperature. The catalytic hydroboration tolerates functionality typically susceptible to insertion, reduction, or cleavage reactions. Turnover numbers (TON) up to 10 000 are observed for aliphatic esters. Lanthanum hydrides, generated by reactions with pinacolborane, are competent for reduction of ketones but are inert toward esters. Instead, catalytic reduction of esters requires activation of the lanthanum hydride by pinacolborane.},

  doi          = {10.1002/ange.201813305},

  journal      = {Angewandte Chemie},

  number       = 8,

  volume       = 131,

  place        = {Germany},

  year         = {Fri Jan 25 00:00:00 EST 2019},

  month        = {Fri Jan 25 00:00:00 EST 2019}

}

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Title: Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage

Abstract

Citation Formats

Highly Selective Hydroboration of Alkenes, Ketones and Aldehydes Catalyzed by a Well-Defined Manganese Complex journal, October 2016

Homoleptic iron( ii ) and cobalt( ii ) bis(phosphoranimide) complexes for the selective hydrofunctionalization of unsaturated molecules journal, January 2017

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Metal–Organic Frameworks Stabilize Solution-Inaccessible Cobalt Catalysts for Highly Efficient Broad-Scope Organic Transformations journal, February 2016

Magnesium-Catalyzed Hydroboration of Pyridines journal, November 2011

Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes journal, August 2017

Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds journal, August 2016

Tris(cyclopentadienyl)lanthanide Complexes as Catalysts for Hydroboration Reaction toward Aldehydes and Ketones journal, June 2017

Homoleptic Trivalent Tris(alkyl) Rare Earth Compounds journal, November 2017

σ-Borane and Dihydroborate Complexes of Ruthenium journal, May 2002

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Magnesium amide catalyzed selective hydroboration of esters journal, January 2017

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Magnesium-catalysed nitrile hydroboration journal, January 2016

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journal, April 2018

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journal, February 2016

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journal, November 2011

Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes
journal, August 2017

Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds
journal, August 2016

Tris(cyclopentadienyl)lanthanide Complexes as Catalysts for Hydroboration Reaction toward Aldehydes and Ketones
journal, June 2017

Homoleptic Trivalent Tris(alkyl) Rare Earth Compounds
journal, November 2017

σ-Borane and Dihydroborate Complexes of Ruthenium
journal, May 2002

Magnesium hydridotriphenylborate [Mg(thf) ₆ ][HBPh ₃ ] ₂ : a versatile hydroboration catalyst
journal, January 2016

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journal, January 2012

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journal, January 2014

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journal, October 2017

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journal, January 2013

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journal, April 2016

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journal, April 2009

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journal, January 2017

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journal, November 2015

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journal, January 2012

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journal, August 2016

Reactivity of Yttrium Methyl Complexes: Hydrido Transfer Capability of Selected Alkylalanes
journal, November 2014

Reactivity of a Molecular Magnesium Hydride Featuring a Terminal Magnesium–Hydrogen Bond
journal, December 2016

Titanocene(II)-Catalyzed Hydroboration of Carbonyl Compounds
journal, December 2012

Magnesium-catalysed nitrile hydroboration
journal, January 2016

Atom-efficient regioselective 1,2-dearomatization of functionalized pyridines by an earth-abundant organolanthanide catalyst
journal, October 2014

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journal, October 2016

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journal, November 2017

σ-Borane Complexes of Iridium: Synthesis and Structural Characterization
journal, August 2008

Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst
journal, January 2017

Activation of Epoxides by a Cooperative Iron–Thiolate Catalyst: Intermediacy of Ferrous Alkoxides in Catalytic Hydroboration
journal, October 2017

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