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Literature DB >> 19899086

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

Abstract

Monocoordinated palladium catalysts derived from sterically hindered, electron-rich phosphines or N-heterocyclic carbenes have revolutionized the Suzuki-Miyaura coupling reaction. The emergence of organotrifluoroborates has provided important new perspectives for the organoboron component of these reactions. In combination, these two components prove to be extraordinarily powerful partners for cross-coupling reactions.

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Year: 2009 PMID： 19899086 PMCID： PMC2917751 DOI： 10.1002/anie.200904306

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

101 in total

1. Beta-aminoethyltrifluoroborates: efficient aminoethylations via Suzuki-Miyaura cross-coupling.

Authors: Gary A Molander; Fabricio Vargas
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

2. 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

3. Monoligated palladium species as catalysts in cross-coupling reactions.

Authors: Ute Christmann; Ramón Vilar
Journal: Angew Chem Int Ed Engl Date: 2005-01-07 Impact factor: 15.336

4. Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.

Authors: Spencer D Dreher; Siang-Ee Lim; Deidre L Sandrock; Gary A Molander
Journal: J Org Chem Date: 2009-05-15 Impact factor: 4.354

5. Atroposelective biaryl coupling with chiral catalysts: total synthesis of the antileishmanial naphthylisoquinoline alkaloids ancistrotanzanine B and ancistroealaine A.

Authors: Gerhard Bringmann; Andreas Hamm; Michaela Schraut
Journal: Org Lett Date: 2003-08-07 Impact factor: 6.005

6. Room-temperature activation of aryl chlorides in Suzuki-Miyaura coupling using a [Pd(micro-Cl)Cl(NHC)]2 complex (NHC = N-heterocyclic carbene).

Authors: Olivier Diebolt; Pierre Braunstein; Steven P Nolan; Catherine S J Cazin
Journal: Chem Commun (Camb) Date: 2008-05-12 Impact factor: 6.222

7. Scope of the Suzuki-Miyaura aminoethylation reaction using organotrifluoroborates.

Authors: Gary A Molander; Ludivine Jean-Gérard
Journal: J Org Chem Date: 2007-10-04 Impact factor: 4.354

8. Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors: Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal: J Org Chem Date: 2009-02-06 Impact factor: 4.354

9. Functionalization of organotrifluoroborates: reductive amination.

Authors: Gary A Molander; David J Cooper
Journal: J Org Chem Date: 2008-04-16 Impact factor: 4.354

10. Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides.

Authors: Gary A Molander; Belgin Canturk
Journal: Org Lett Date: 2008-04-26 Impact factor: 6.005

37 in total

Review 1. Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors: Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal: Chem Rev Date: 2010-12-06 Impact factor: 60.622

2. Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Authors: Deidre L Sandrock; Ludivine Jean-Gérard; Cheng-yi Chen; Spencer D Dreher; Gary A Molander
Journal: J Am Chem Soc Date: 2010-11-15 Impact factor: 15.419

3. Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides.

Authors: Gary A Molander; O Andreea Argintaru; Ioana Aron; Spencer D Dreher
Journal: Org Lett Date: 2010-11-19 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. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

6. Scope of the two-step, one-pot palladium-catalyzed borylation/Suzuki cross-coupling reaction utilizing bis-boronic acid.

Authors: Gary A Molander; Sarah L J Trice; Steven M Kennedy
Journal: J Org Chem Date: 2012-09-20 Impact factor: 4.354

7. Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors: David S Surry; Stephen L Buchwald
Journal: Chem Sci Date: 2011 Impact factor: 9.825

8. Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors: Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: Org Lett Date: 2013-03-15 Impact factor: 6.005

9. A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid.

Authors: Gary A Molander; Sarah L J Trice; Brittany Tschaen
Journal: Tetrahedron Date: 2015-09-02 Impact factor: 2.457

10. Synthesis and minisci reactions of organotrifluoroborato building blocks.

Authors: Marc Presset; Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal: J Org Chem Date: 2013-04-17 Impact factor: 4.354