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Literature DB >> 28796936

Allyl-Palladium-Catalyzed α,β-Dehydrogenation of Carboxylic Acids via Enediolates.

Yizhou Zhao¹, Yifeng Chen^1,2, Timothy R Newhouse¹.

Abstract

A highly practical and step-economic α,β-dehydrogenation of carboxylic acids via enediolates is reported through the use of allyl-palladium catalysis. Dianions underwent smooth dehydrogenation when generated using Zn(TMP)2 ⋅2 LiCl as a base in the presence of excess ZnCl2 , thus avoiding the typical decarboxylation pathway of these substrates. Direct access to 2-enoic acids allows derivatization by numerous approaches.

Entities: Chemical

Keywords: carbanions; carboxylic acids; dehydrogenation; palladium; synthetic methods

Year: 2017 PMID： 28796936 DOI： 10.1002/anie.201706893

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

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Cited

7 in total

1. Analysis of chain length, substitution patterns, and unsaturation of AM-404 derivatives as 20S proteasome stimulators.

Authors: Rachel A Coleman; Christine S Muli; Yizhou Zhao; Atul Bhardwaj; Timothy R Newhouse; Darci J Trader
Journal: Bioorg Med Chem Lett Date: 2018-12-19 Impact factor: 2.823

2. Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand.

Authors: Tyler J Fulton; Brenda Wu; Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal: Tetrahedron Date: 2019-06-01 Impact factor: 2.457

Allyl-Palladium-Catalyzed α,β-Dehydrogenation of Carboxylic Acids via Enediolates.

1. Analysis of chain length, substitution patterns, and unsaturation of AM-404 derivatives as 20S proteasome stimulators.

2. Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand.

3. Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation.

4. Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones.

5. Dehydrogenative Pd and Ni Catalysis for Total Synthesis.

6. Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C-H activation.

7. Chemoselective α,β-Dehydrogenation of Saturated Amides.