Literature DB >> 16671774

Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.

Gary A Molander1, Jungyeob Ham.   

Abstract

[reaction: see text] Potassium bromo- and iodomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF(2). Moreover, a new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of the halide in these potassium halomethyltrifluoroborates is described.

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Year:  2006        PMID: 16671774      PMCID: PMC2528247          DOI: 10.1021/ol060375a

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

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3.  Hydroboration with pyridine borane at room temperature.

Authors:  Julia M Clay; Edwin Vedejs
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4.  Asymmetric homologation of boronic esters bearing azido and silyloxy substituents.

Authors:  R P Singh; D S Matteson
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

5.  Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates.

Authors:  G A Molander; T Ito
Journal:  Org Lett       Date:  2001-02-08       Impact factor: 6.005

6.  Regiospecific functionalization of methyl C-H bonds of alkyl groups in reagents with heteroatom functionality.

Authors:  Joshua D Lawrence; Makoto Takahashi; Chulsung Bae; John F Hartwig
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

7.  A facile one-pot synthesis of alkyl aryl sulfides from aryl bromides.

Authors:  Jungyeob Ham; Inho Yang; Heonjoong Kang
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8.  Design, synthesis, and evaluation of novel boronic-chalcone derivatives as antitumor agents.

Authors:  Srinivas K Kumar; Erin Hager; Catherine Pettit; Hallur Gurulingappa; Nancy E Davidson; Saeed R Khan
Journal:  J Med Chem       Date:  2003-07-03       Impact factor: 7.446

  8 in total
  23 in total

1.  Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

Authors:  Gary A Molander; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates.

Authors:  Fei Liu; Todd Evans; Bhaskar C Das
Journal:  Tetrahedron Lett       Date:  2008-03-03       Impact factor: 2.415

3.  Preparation and wittig reactions of organotrifluoroborato phosphonium ylides.

Authors:  Gary A Molander; Jungyeob Ham; Belgin Canturk
Journal:  Org Lett       Date:  2007-02-06       Impact factor: 6.005

Review 4.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

5.  Facile synthesis of borofragments and their evaluation in activity-based protein profiling.

Authors:  Shinya Adachi; Armand B Cognetta; Micah J Niphakis; Zhi He; Adam Zajdlik; Jeffrey D St Denis; Conor C G Scully; Benjamin F Cravatt; Andrei K Yudin
Journal:  Chem Commun (Camb)       Date:  2015-02-28       Impact factor: 6.222

6.  Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

7.  Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates.

Authors:  Gary A Molander; Nicolas Fleury-Brégeot; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2011-03-02       Impact factor: 6.005

8.  A novel route to organonitrites by Pd-catalyzed cross-coupling of sodium nitrite and potassium organotrifluoroborates.

Authors:  Mohammad Al-Masum; Nabil Saleh; Tasfia Islam
Journal:  Tetrahedron Lett       Date:  2013-02-01       Impact factor: 2.415

9.  Facile synthesis of highly functionalized ethyltrifluoroborates.

Authors:  Gary A Molander; Wilma Febo-Ayala; Montserrat Ortega-Guerra
Journal:  J Org Chem       Date:  2008-06-28       Impact factor: 4.354

10.  (1)H, (13)C, (19)F and (11)B NMR spectral reference data of some potassium organotrifluoroborates.

Authors:  Roberta A Oliveira; Ricardo O Silva; Gary A Molander; Paulo H Menezes
Journal:  Magn Reson Chem       Date:  2009-10       Impact factor: 2.447

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