Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis

Junor, Glen P.; Romero, Erik A.; Chen, Xi; Jazzar, Rodolphe; Bertrand, Guy

doi:10.1002/ange.201814081

Title: Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis

Authors:

^[1];

^[1]

UCSD-CNRS Joint Research Laboratory (UMI 3555) Department of Chemistry and Biochemistry University of California San Diego, La Jolla CA 92093-0358 USA

Publication Date:: 2019-02-06

Sponsoring Org.:: USDOE

OSTI Identifier:: 1493818

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Angewandte Chemie

Additional Journal Information:: Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 9; Journal ID: ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Citation Formats


                    Junor, Glen P., Romero, Erik A., Chen, Xi, Jazzar, Rodolphe, and Bertrand, Guy. Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis.  Germany: N. p., 2019. 
Web.  doi:10.1002/ange.201814081.

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                    Junor, Glen P., Romero, Erik A., Chen, Xi, Jazzar, Rodolphe, & Bertrand, Guy. Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis.  Germany.  https://doi.org/10.1002/ange.201814081

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                    Junor, Glen P., Romero, Erik A., Chen, Xi, Jazzar, Rodolphe, and Bertrand, Guy. Wed .  
"Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis".  Germany.  https://doi.org/10.1002/ange.201814081.

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@article{osti_1493818,

  title        = {Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis},

  author       = {Junor, Glen P. and Romero, Erik A. and Chen, Xi and Jazzar, Rodolphe and Bertrand, Guy},

  abstractNote = {},

  doi          = {10.1002/ange.201814081},

  journal      = {Angewandte Chemie},

  number       = 9,

  volume       = 131,

  place        = {Germany},

  year         = {2019},

  month        = {2}

}

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Title: Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis

Citation Formats

Catalyst-free dehydrocoupling of amines, alcohols, and thiols with pinacol borane and 9-borabicyclononane (9-BBN) journal, January 2016

Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives journal, June 2017

Alkoxide Activation of Aminoboranes towards Selective Amination journal, September 2013

Diastereo- and Enantioselective Synthesis of β-Aminoboronate Esters by Copper(I)-Catalyzed 1,2-Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines journal, August 2017

Application of a robustness screen for the evaluation of synthetic organic methodology journal, May 2014

Solid Supported Chiral N -Picolylimidazolidinones: Recyclable Catalysts for the Enantioselective, Metal- and Hydrogen-Free Reduction of Imines in Batch and in Flow Mode journal, June 2017

A Tethered Ru-S Complex with an Axial Chiral Thiolate Ligand for Cooperative Si-H Bond Activation: Application to Enantioselective Imine Reduction journal, March 2017

Transition-metal-free B–B and B–interelement reactions with organic molecules journal, January 2017

Pitfalls in Computational Modeling of Chemical Reactions and How To Avoid Them journal, September 2018

Synthesis and Anti-inflammatory Evaluation of 2-Aminobenzaldehydes via Ir(III)-Catalyzed C–H Amidation of Aldimines with Acyl Azides journal, June 2017

Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes journal, February 1997

Acid-Free, Aminoborane-Mediated Ugi-Type Reaction Leading to General Utilization of Secondary Amines journal, October 2007

Template-directed synthesis employing reversible imine bond formation journal, January 2007

Aminoboration: Addition of B–N σ Bonds across C–C π Bonds journal, August 2015

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls journal, July 2017

A complete basis set model chemistry. II. Open‐shell systems and the total energies of the first‐row atoms journal, May 1991

Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules journal, August 2006

Aminoboranes as new iminium ion generators in amination reactions journal, January 2006

Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H 2 journal, May 2018

XSEDE: Accelerating Scientific Discovery journal, September 2014

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals journal, July 2007

trans -Aminoboration across Internal Alkynes Catalyzed by B(C 6 F 5 ) 3 for the Synthesis of Borylated Indoles journal, March 2017

A General Aminocatalytic Method for the Synthesis of Aldimines journal, January 2014

Ynones Merge Activation/Conjugate Addition of Chalcogenoborates ArE-Bpin (E=Se, S) journal, October 2015

Diastereo- and Enantioselective Synthesis of β-Aminoboronate Esters by Copper(I)-Catalyzed 1,2-Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines journal, August 2017

Alkoxide Activation of Aminoboranes towards Selective Amination journal, September 2013

Aminoboranes as “Compatible” Iminium Ion Generators in Aminative C−C Bond Formations journal, October 2004

Additions of Organometallic Reagents to CN Bonds: Reactivity and Selectivity journal, June 1998

Enantio- and Diastereoselective Synthesis of 1,5- syn -( Z )-Amino Alcohols via Imine Double Allylboration: Synthesis of trans -1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine journal, May 2017

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Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid journal, January 2018

An Unprecedented Pseudo-[3+2] Annulation between N -(4-Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole-2,4-dialdehydes : An Unprecedented Pseudo-[3+2] Annulation between journal, May 2017

Dynamic imine chemistry journal, January 2012

A robustness screen for the rapid assessment of chemical reactions journal, June 2013

Chloroboration and allied reactions of unsaturated compounds. Part IV. Boration of di-p-tolylcarbodi-imide journal, January 1966

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls journal, July 2017

Catalyst-free dehydrocoupling of amines, alcohols, and thiols with pinacol borane and 9-borabicyclononane (9-BBN)
journal, January 2016

Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives
journal, June 2017

Alkoxide Activation of Aminoboranes towards Selective Amination
journal, September 2013

Diastereo- and Enantioselective Synthesis of β-Aminoboronate Esters by Copper(I)-Catalyzed 1,2-Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines
journal, August 2017

Application of a robustness screen for the evaluation of synthetic organic methodology
journal, May 2014

Solid Supported Chiral N -Picolylimidazolidinones: Recyclable Catalysts for the Enantioselective, Metal- and Hydrogen-Free Reduction of Imines in Batch and in Flow Mode
journal, June 2017

A Tethered Ru-S Complex with an Axial Chiral Thiolate Ligand for Cooperative Si-H Bond Activation: Application to Enantioselective Imine Reduction
journal, March 2017

Transition-metal-free B–B and B–interelement reactions with organic molecules
journal, January 2017

Pitfalls in Computational Modeling of Chemical Reactions and How To Avoid Them
journal, September 2018

Synthesis and Anti-inflammatory Evaluation of 2-Aminobenzaldehydes via Ir(III)-Catalyzed C–H Amidation of Aldimines with Acyl Azides
journal, June 2017

Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes
journal, February 1997

Acid-Free, Aminoborane-Mediated Ugi-Type Reaction Leading to General Utilization of Secondary Amines
journal, October 2007

Template-directed synthesis employing reversible imine bond formation
journal, January 2007

Aminoboration: Addition of B–N σ Bonds across C–C π Bonds
journal, August 2015

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls
journal, July 2017

A complete basis set model chemistry. II. Open‐shell systems and the total energies of the first‐row atoms
journal, May 1991

Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules
journal, August 2006

Aminoboranes as new iminium ion generators in amination reactions
journal, January 2006

Main-Group-Catalyzed Reductive Alkylation of Multiply Substituted Amines with Aldehydes Using H ₂
journal, May 2018

XSEDE: Accelerating Scientific Discovery
journal, September 2014

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007

trans -Aminoboration across Internal Alkynes Catalyzed by B(C ₆ F ₅ ) ₃ for the Synthesis of Borylated Indoles
journal, March 2017

A General Aminocatalytic Method for the Synthesis of Aldimines
journal, January 2014

Ynones Merge Activation/Conjugate Addition of Chalcogenoborates ArE-Bpin (E=Se, S)
journal, October 2015

Diastereo- and Enantioselective Synthesis of β-Aminoboronate Esters by Copper(I)-Catalyzed 1,2-Addition of 1,1-Bis[(pinacolato)boryl]alkanes to Imines
journal, August 2017

Alkoxide Activation of Aminoboranes towards Selective Amination
journal, September 2013

Aminoboranes as “Compatible” Iminium Ion Generators in Aminative C−C Bond Formations
journal, October 2004

Additions of Organometallic Reagents to CN Bonds: Reactivity and Selectivity
journal, June 1998

Enantio- and Diastereoselective Synthesis of 1,5- syn -( Z )-Amino Alcohols via Imine Double Allylboration: Synthesis of trans -1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
journal, May 2017

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection
journal, April 2004

394. Chloroboration and allied reactions of unsaturated compounds. Part III. Aminoboration and alkoxyboration of isocyanates and isothiocyanates
journal, January 1964

Chemo- and Stereoselective Crotylation of Aldehydes and Cyclic Aldimines with Allylic gem -Diboronate Ester
journal, July 2017

Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid
journal, January 2018

An Unprecedented Pseudo-[3+2] Annulation between N -(4-Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole-2,4-dialdehydes : An Unprecedented Pseudo-[3+2] Annulation between
journal, May 2017

Dynamic imine chemistry
journal, January 2012

A robustness screen for the rapid assessment of chemical reactions
journal, June 2013

Chloroboration and allied reactions of unsaturated compounds. Part IV. Boration of di-p-tolylcarbodi-imide
journal, January 1966

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls
journal, July 2017