Literature DB >> 11428022

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

G A Molander1, T Ito.   

Abstract

[figure: see text] The palladium-catalyzed coupling reaction of potassium alkyltrifluoroborates with aryl- or alkenyltriflates proceeds to afford the corresponding arenes or alkenes in high yield. The borates are all solids, stable in air, and thus can be stored on the shelf indefinitely. The cross coupling can be effected using PdCl2(dppf).CH2Cl2 as the catalyst in THF-H2O in the presence of Cs2CO3. A variety of functional groups can be tolerated within the borate and/or the triflate coupling partner.

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Year:  2001        PMID: 11428022     DOI: 10.1021/ol006896u

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


  21 in total

1.  Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Authors:  Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-08       Impact factor: 15.419

Review 2.  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

3.  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

4.  Hydroboration with pyridine borane at room temperature.

Authors:  Julia M Clay; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

5.  Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling.

Authors:  Ping Zhang; Hai Le; Robert E Kyne; James P Morken
Journal:  J Am Chem Soc       Date:  2011-06-07       Impact factor: 15.419

6.  The organocatalytic three-step total synthesis of (+)-frondosin B.

Authors:  Maud Reiter; Staffan Torssell; Sandra Lee; David W C Macmillan
Journal:  Chem Sci       Date:  2010-07       Impact factor: 9.825

7.  Copper-mediated N-Arylation of Methyl 2-Aminothiophene-3-carboxylate with Organoboron Reagents.

Authors:  Komal Rizwan; Idris Karakaya; Drew Heitz; Muhammad Zubair; Nasir Rasool; Gary A Molander
Journal:  Tetrahedron Lett       Date:  2015-12-09       Impact factor: 2.415

8.  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

9.  Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides--reaction discovery using parallel microscale experimentation.

Authors:  Spencer D Dreher; Peter G Dormer; Deidre L Sandrock; Gary A Molander
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

10.  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

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