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Literature DB >> 22263870

Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates.

Alison E Metz¹, Simon Berritt, Spencer D Dreher, Marisa C Kozlowski.

Abstract

Palladium-catalyzed cross-coupling conditions were developed that efficiently afford 2-aryl-2-nitroacetates from aryl bromides and the very acidic nitroacetates.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2012 PMID： 22263870 PMCID： PMC3289998 DOI： 10.1021/ol203303b

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

15 in total

1. Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: understanding ligand effects.

Authors: Carlos H Burgos; Timothy E Barder; Xiaohua Huang; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2006-06-26 Impact factor: 15.336

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. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

Review 4. Palladium-catalysed hydroxylation and alkoxylation.

Authors: Stephan Enthaler; Anna Company
Journal: Chem Soc Rev Date: 2011-06-06 Impact factor: 54.564

5. Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands.

Authors: Neil A Beare; John F Hartwig
Journal: J Org Chem Date: 2002-01-25 Impact factor: 4.354

6. Palladium-catalyzed monoarylation of nitroalkanes.

Authors: Erasmus M Vogl; Stephen L Buchwald
Journal: J Org Chem Date: 2002-01-11 Impact factor: 4.354

7. Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.

Authors: Fabio Bellina; Renzo Rossi
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

8. Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

Authors: Xuebin Liao; Zhiqiang Weng; John F Hartwig
Journal: J Am Chem Soc Date: 2007-12-13 Impact factor: 15.419

9. Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Authors: Darcy A Culkin; John F Hartwig
Journal: Acc Chem Res Date: 2003-04 Impact factor: 22.384

Review 10. Transition metal catalyzed synthesis of aryl sulfides.

Authors: Chad C Eichman; James P Stambuli
Journal: Molecules Date: 2011-01-17 Impact factor: 4.411

9 in total

1. Accounting for Strong Ligand Sensitivity in Pd-Catalyzed α-Arylation of Enolates from Ketones, Esters, and Nitroalkanes.

Authors: Sergei Tcyrulnikov; Marisa C Kozlowski
Journal: J Org Chem Date: 2020-02-12 Impact factor: 4.354

Efficient palladium-catalyzed cross-coupling of highly acidic substrates, nitroacetates.

1. Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: understanding ligand effects.

Review 2. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

3. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Review 4. Palladium-catalysed hydroxylation and alkoxylation.

5. Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands.

6. Palladium-catalyzed monoarylation of nitroalkanes.

7. Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.

8. Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

9. Palladium-catalyzed alpha-arylation of carbonyl compounds and nitriles.

Review 10. Transition metal catalyzed synthesis of aryl sulfides.

1. Accounting for Strong Ligand Sensitivity in Pd-Catalyzed α-Arylation of Enolates from Ketones, Esters, and Nitroalkanes.

2. Regioselective alkylation of 2,4-dihydroxybenzyaldehydes and 2,4-dihydroxyacetophenones.

3. 2-Aryl-2-nitroacetates as central precursors to aryl nitromethanes, α-ketoesters, and α-amino acids.

4. Palladium-catalyzed nitromethylation of aryl halides: an orthogonal formylation equivalent.

5. Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides.

6. Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner-Wadsworth-Emmons Olefination.

7. Palladium-Catalyzed α-Arylation of Aryl Nitromethanes.

8. Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.

Review 9. Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems.