Literature DB >> 18412389

Functionalization of organotrifluoroborates: reductive amination.

Gary A Molander1, David J Cooper.   

Abstract

Herein we report the conversion of aldehyde-containing potassium and tetrabutylammonium organotrifluoroborates to the corresponding amines through reductive amination protocols. Potassium formate facilitated by catalytic palladium acetate, sodium triacetoxyborohydride, and pyridine borane have all served as effective hydride donors, reducing the initially formed imines or iminium ions to provide the corresponding amines.

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Year:  2008        PMID： 18412389      PMCID： PMC2819055          DOI： 10.1021/jo800383e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  17 in total

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4.  Synthesis of unsaturated organotrifluoroborates via Wittig and Horner-Wadsworth-Emmons olefination.

Authors:  Gary A Molander; Ruth Figueroa
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

5.  Fragmentation of carbonyl oxides by N-oxides: an improved approach to alkene ozonolysis.

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6.  Reactivity of stable trifluoroacetaldehyde hemiaminals. 2. Generation and synthetic potentialities of fluorinated iminiums.

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9.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates.

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Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

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  8 in total

1.  Metal-free chlorodeboronation of organotrifluoroborates.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2011-08-03       Impact factor: 4.354

2.  Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence.

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Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

3.  Oxidation of organotrifluoroborates via oxone.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

4.  Oxidative condensations to form benzimidazole-substituted potassium organotrifluoroborates.

Authors:  Gary A Molander; Kehinde Ajayi
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

5.  Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases.

Authors:  Sebastian A Testero; Renee Bouley; Jed F Fisher; Mayland Chang; Shahriar Mobashery
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6.  Raman Spectroscopic and Quantum Chemical Investigation of the Pyridine-Borane Complex and the Effects of Dative Bonding on the Normal Modes of Pyridine.

Authors:  Ethan C Lambert; Benjamin W Stratton; Nathan I Hammer
Journal:  ACS Omega       Date:  2022-04-08

7.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Efficient hydrolysis of organotrifluoroborates via silica gel and water.

Authors:  Gary A Molander; Livia N Cavalcanti; Belgin Canturk; Po-Shen Pan; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354
  8 in total

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