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Literature DB >> 30673257

One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp²-Sp³ Cross-Coupling.

Takaoki Koyanagi¹, Ananda Herath¹, Ashley Chong¹, Maxim Ratnikov¹, Andrew Valiere¹, Jim Chang¹, Valentina Molteni¹, Jon Loren¹.

Abstract

A one-pot electrochemical nickel-catalyzed decarboxylative sp2-sp3 cross-coupling reaction has been developed using redox-active esters prepared in situ from alkyl carboxylates and N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (PITU). This undivided cell one-pot method enables C-C bond formation using inexpensive, benchtop-stable reagents with isolated yields up to 95% with good functional group tolerance, which includes nitrile, ketone, ester, alkene and selectivity over other aromatic halogens.

Entities: Chemical Gene

Year: 2019 PMID： 30673257 DOI： 10.1021/acs.orglett.8b04090

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

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Cited

16 in total

1. Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis.

Authors: Travis J DeLano; Sarah E Reisman
Journal: ACS Catal Date: 2019-07-25 Impact factor: 13.084

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

One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp²-Sp³ Cross-Coupling.

1. Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis.

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

3. Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters.

4. Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

5. In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl Halides.

6. Convergent Synthesis of (R)-Silodosin via Decarboxylative Cross-Coupling.

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

8. Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds.

9. Carboxylate breaks the arene C-H bond via a hydrogen-atom-transfer mechanism in electrochemical cobalt catalysis.

10. ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand.