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Literature DB >> 30252190

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis.

Xu-Ge Liu¹, Chu-Jun Zhou¹, E Lin¹, Xiang-Lei Han¹, Shang-Shi Zhang¹, Qingjiang Li¹, Honggen Wang¹.

Abstract

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl-aryl, alkyl-alkenyl, and alkyl-alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

Entities: Chemical

Keywords: C−C bond formation; Negishi coupling; cobalt; decarboxylation; redox-active esters

Year: 2018 PMID： 30252190 DOI： 10.1002/anie.201806799

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

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Cited

12 in total

1. Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

Authors: Tie-Gen Chen; Haolin Zhang; Pavel K Mykhailiuk; Rohan R Merchant; Courtney A Smith; Tian Qin; Phil S Baran
Journal: Angew Chem Int Ed Engl Date: 2019-01-30 Impact factor: 15.336

2. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors: Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal: J Am Chem Soc Date: 2019-04-16 Impact factor: 15.419

3. Activator-free single-component Co(I)-catalysts for regio- and enantioselective heterodimerization and hydroacylation reactions of 1,3-dienes. New reduction procedures for synthesis of [L]Co(I)-complexes and comparison to in situ generated catalysts.

Authors: Mahesh M Parsutkar; Curtis E Moore; T V RajanBabu
Journal: Dalton Trans Date: 2022-07-05 Impact factor: 4.569

4. Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

Authors: Giulio Bertuzzi; Giada Ombrosi; Marco Bandini
Journal: Org Lett Date: 2022-06-14 Impact factor: 6.072

5. Nickel-Catalyzed C(sp³)-C(sp³) Cross-Electrophile Coupling of In Situ Generated NHP Esters with Unactivated Alkyl Bromides.

Authors: Kai Kang; Daniel J Weix
Journal: Org Lett Date: 2022-04-13 Impact factor: 6.072

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis.

1. Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

2. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

3. Activator-free single-component Co(I)-catalysts for regio- and enantioselective heterodimerization and hydroacylation reactions of 1,3-dienes. New reduction procedures for synthesis of [L]Co(I)-complexes and comparison to in situ generated catalysts.

4. Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

5. Nickel-Catalyzed C(sp³)-C(sp³) Cross-Electrophile Coupling of In Situ Generated NHP Esters with Unactivated Alkyl Bromides.

6. Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

7. Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.

8. Electrochemical Nozaki-Hiyama-Kishi Coupling: Scope, Applications, and Mechanism.

9. The Asymmetric Synthesis of Amines via Nickel-Catalyzed Enantioconvergent Substitution Reactions.

10. Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes.