Literature DB >> 18393522

Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates.

Gary A Molander1, Daniel E Petrillo.   

Abstract

Ketone-, ester-, and amide-containing potassium trifluoroboratohomoenolates were prepared in good to excellent yields from the corresponding unsaturated carbonyl compounds. They were shown to be effective coupling partners in the Suzuki-Miyaura reaction with a variety of electrophiles including electron-rich and electron-poor aryl bromides and -chlorides.

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Year:  2008        PMID: 18393522     DOI: 10.1021/ol800357c

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


  17 in total

1.  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

2.  Synthesis of tetranor-PGE1: a urinary metabolite of prostaglandins E1 and E2.

Authors:  Jennifer R Kimbrough; Somnath Jana; Kwangho Kim; Alexander Allweil; John A Oates; Ginger L Milne; Gary A Sulikowski
Journal:  Tetrahedron Lett       Date:  2020-04-10       Impact factor: 2.415

3.  Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane.

Authors:  Gary A Molander; Silas A McKee
Journal:  Org Lett       Date:  2011-08-05       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 Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

Authors:  Gary A Molander; Inji Shin; Ludivine Jean-Gérard
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

6.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

7.  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

8.  Use of potassium beta-trifluoroborato amides in Suzuki-Miyaura cross-coupling reactions.

Authors:  Gary A Molander; Ludivine Jean-Gérard
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

9.  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

Review 10.  Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11
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