Literature DB >> 18321102

Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates.

Haibo Ge1, Micah J Niphakis, Gunda I Georg.   

Abstract

A Pd(II)-catalyzed reaction for the direct arylation of cyclic enaminones is reported. The reactivity of electron-rich, electron-poor, and sterically encumbered organotrifluoroborates was investigated. This reaction represents a unique use for organotrifluoroborates as coupling partners and discloses the utility of enaminones for direct-functionalization reactions. It provides immediate access to arylpiperidine, indolizidine, and quinolizidine scaffolds from the corresponding mono- and bicyclic, unattenuated enaminones.

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Year:  2008        PMID： 18321102     DOI： 10.1021/ja710221c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

1.  Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors:  Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

2.  Direct Hiyama cross-coupling of enaminones with triethoxy(aryl)silanes and dimethylphenylsilanol.

Authors:  Lei Bi; Gunda I Georg
Journal:  Org Lett       Date:  2011-09-22       Impact factor: 6.005

3.  Palladium-Catalyzed C-H Arylation Using Aryltrifluoroborates in Conjunction with a MnIII Oxidant under Mild Conditions.

Authors:  Cydney K Seigerman; Tiffiny M Micyus; Sharon R Neufeldt; Melanie S Sanford
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

4.  A Sequential Cycloaddition Strategy for the Synthesis of Alsmaphorazine B Traces a Path Through a Family of Alstonia Alkaloids.

Authors:  Allen Y Hong; Christopher D Vanderwal
Journal:  Tetrahedron       Date:  2016-11-03       Impact factor: 2.457

5.  Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

Authors:  Keary M Engle; Peter S Thuy-Boun; Michael Dang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

6.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

7.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

8.  Reaction between enaminones and acetylenic esters in the presence of triphenylphosphine: a convenient synthesis of alkyl 2(1-benzyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)acetates.

Authors:  Farough Nasiri; Massood Bayzidi; Amin Zolali
Journal:  Mol Divers       Date:  2012-08-25       Impact factor: 2.943

9.  Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

Authors:  Yi-Yun Yu; Lei Bi; Gunda I Georg
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

10.  Regioselective C5-alkylation and C5-methylcarbamate formation of 2,3-dihydro-4-pyridones and C3-alkylation and C3-methylcarbamate formation of 4-(pyrrolidin-1-yl)furan-2(5H)-one.

Authors:  Xingxian Gu; Gunda I Georg
Journal:  Tetrahedron Lett       Date:  2015-10-21       Impact factor: 2.415
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