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

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
  1. UCSD-CNRS Joint Research Laboratory (UMI 3555)Department of Chemistry and BiochemistryUniversity of California San Diego, La Jolla CA 92093-0358 USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1493818
Grant/Contract Number:  
SC0009376
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.
Junor, Glen P., Romero, Erik A., Chen, Xi, Jazzar, Rodolphe, & Bertrand, Guy. Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis. Germany. doi:10.1002/ange.201814081.
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. doi:10.1002/ange.201814081.
@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}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/ange.201814081

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Works referenced in this record:

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

  • Romero, Erik A.; Peltier, Jesse L.; Jazzar, Rodolphe
  • Chemical Communications, Vol. 52, Issue 69
  • DOI: 10.1039/C6CC06096J

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

  • Alonso, Concepción; González, María; Palacios, Francisco
  • The Journal of Organic Chemistry, Vol. 82, Issue 12
  • DOI: 10.1021/acs.joc.7b00977

Alkoxide Activation of Aminoboranes towards Selective Amination
journal, September 2013

  • Solé, Cristina; Fernández, Elena
  • Angewandte Chemie International Edition, Vol. 52, Issue 43
  • DOI: 10.1002/anie.201305098

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

  • Collins, Karl D.; Rühling, Andreas; Glorius, Frank
  • Nature Protocols, Vol. 9, Issue 6
  • DOI: 10.1038/nprot.2014.076

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

  • Porta, Riccardo; Benaglia, Maurizio; Annunziata, Rita
  • Advanced Synthesis & Catalysis, Vol. 359, Issue 14
  • DOI: 10.1002/adsc.201700376

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

  • Wübbolt, Simon; Maji, Modhu Sudan; Irran, Elisabeth
  • Chemistry - A European Journal, Vol. 23, Issue 25
  • DOI: 10.1002/chem.201700304

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

  • Cuenca, Ana B.; Shishido, Ryosuke; Ito, Hajime
  • Chemical Society Reviews, Vol. 46, Issue 2
  • DOI: 10.1039/C6CS00692B

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

  • Kim, Saegun; Chakrasali, Prashant; Suh, Hyo Sun
  • The Journal of Organic Chemistry, Vol. 82, Issue 14
  • DOI: 10.1021/acs.joc.7b01280

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

  • Noyori, Ryoji; Hashiguchi, Shohei
  • Accounts of Chemical Research, Vol. 30, Issue 2
  • DOI: 10.1021/ar9502341

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

  • Tanaka, Yusuke; Hasui, Tomoaki; Suginome, Michinori
  • Organic Letters, Vol. 9, Issue 22
  • DOI: 10.1021/ol701570c

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

  • Meyer, Cari D.; Joiner, C. Steven; Stoddart, J. Fraser
  • Chemical Society Reviews, Vol. 36, Issue 11
  • DOI: 10.1039/b513441m

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

  • Chong, Eugene; Blum, Suzanne A.
  • Journal of the American Chemical Society, Vol. 137, Issue 32
  • DOI: 10.1021/jacs.5b06678

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

  • Petersson, G. A.; Al‐Laham, Mohammad A.
  • The Journal of Chemical Physics, Vol. 94, Issue 9
  • DOI: 10.1063/1.460447

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

  • Hoshimoto, Yoichi; Kinoshita, Takuya; Hazra, Sunit
  • Journal of the American Chemical Society, Vol. 140, Issue 23
  • DOI: 10.1021/jacs.8b03626

XSEDE: Accelerating Scientific Discovery
journal, September 2014

  • Towns, John; Cockerill, Timothy; Dahan, Maytal
  • Computing in Science & Engineering, Vol. 16, Issue 5
  • DOI: 10.1109/MCSE.2014.80

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

  • Morales, Sara; Guijarro, Fernando G.; García Ruano, José Luis
  • Journal of the American Chemical Society, Vol. 136, Issue 3
  • DOI: 10.1021/ja4111418

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

  • Civit, Marc G.; Sanz, Xavier; Vogels, Christopher M.
  • Advanced Synthesis & Catalysis, Vol. 357, Issue 14-15
  • DOI: 10.1002/adsc.201500650

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

  • Kim, Jeongho; Ko, Kwangwook; Cho, Seung Hwan
  • Angewandte Chemie International Edition, Vol. 56, Issue 38
  • DOI: 10.1002/anie.201705829

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

  • Suginome, Michinori; Uehlin, Lars; Murakami, Masahiro
  • Journal of the American Chemical Society, Vol. 126, Issue 41
  • DOI: 10.1021/ja045827y

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


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

  • Cragg, R. H.; Lappert, M. F.; Tilley, B. P.
  • Journal of the Chemical Society (Resumed)
  • DOI: 10.1039/jr9640002108

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

  • Sapsford, Joshua S.; Scott, Daniel J.; Allcock, Nathan J.
  • Advanced Synthesis & Catalysis, Vol. 360, Issue 6
  • DOI: 10.1002/adsc.201701418

Dynamic imine chemistry
journal, January 2012

  • Belowich, Matthew E.; Stoddart, J. Fraser
  • Chemical Society Reviews, Vol. 41, Issue 6
  • DOI: 10.1039/c2cs15305j

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

  • Collins, Karl D.; Glorius, Frank
  • Nature Chemistry, Vol. 5, Issue 7
  • DOI: 10.1038/nchem.1669

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

  • Jefferson, R.; Lappert, M. F.; Prokai, B.
  • Journal of the Chemical Society A: Inorganic, Physical, Theoretical
  • DOI: 10.1039/j19660001584

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

  • Dorkó, Éva; Szabó, Márk; Kótai, Bianka
  • Angewandte Chemie International Edition, Vol. 56, Issue 32
  • DOI: 10.1002/anie.201703591