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Literature DB >> 26790471

Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide.

Yifeng Chen¹, Aneta Turlik¹, Timothy R Newhouse¹.

Abstract

A practical and direct method for the α,β-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.

Entities: Chemical

Year: 2016 PMID： 26790471 DOI： 10.1021/jacs.5b12924

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

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Cited

19 in total

1. Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration.

Authors: Stephanie A Murray; Eugenia C M Luc; Simon J Meek
Journal: Org Lett Date: 2018-01-10 Impact factor: 6.005

2. Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products.

Authors: Andrei V Iosub; Shannon S Stahl
Journal: ACS Catal Date: 2016-10-24 Impact factor: 13.084

3. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

Authors: Padon Chuentragool; Marvin Parasram; Yi Shi; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2018-02-07 Impact factor: 15.419

4. Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

Authors: Mark D Aparece; Chenpeng Gao; Gabriel J Lovinger; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2018-12-12 Impact factor: 15.336

5. 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

Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide.

1. Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration.

2. Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products.

3. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

4. Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

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

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

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

8. Dehydrogenative Pd and Ni Catalysis for Total Synthesis.

9. Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization.

10. Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation*.