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Literature DB >> 12940714

Decarbonylative cross-coupling of cyclic anhydrides: introducing stereochemistry at an sp3 carbon in the cross-coupling event.

Erin M O'Brien¹, Eric A Bercot, Tomislav Rovis.

Abstract

Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event.

Entities: Chemical Gene

Year: 2003 PMID： 12940714 DOI： 10.1021/ja036290b

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

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Cited

10 in total

1. Nickel/zinc-catalyzed decarbonylative addition of anhydrides to alkynes: a DFT study.

Authors: Qingxi Meng; Ming Li
Journal: J Mol Model Date: 2013-08-17 Impact factor: 1.810

2. Synthetic analogs for evaluating the influence of N-H...S hydrogen bonds on the formation of thioester in acetyl coenzyme A synthase.

Authors: Piyal W G Ariyananda; Matthew T Kieber-Emmons; Glenn P A Yap; Charles G Riordan
Journal: Dalton Trans Date: 2009-04-27 Impact factor: 4.390

3. Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides.

Authors: Erin E Stache; Tomislav Rovis; Abigail G Doyle
Journal: Angew Chem Int Ed Engl Date: 2017-02-23 Impact factor: 15.336

4. Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture.

Authors: Chengwei Liu; Michal Szostak
Journal: Org Chem Front Date: 2021-06-22 Impact factor: 5.456

Decarbonylative cross-coupling of cyclic anhydrides: introducing stereochemistry at an sp3 carbon in the cross-coupling event.

1. Nickel/zinc-catalyzed decarbonylative addition of anhydrides to alkynes: a DFT study.

2. Synthetic analogs for evaluating the influence of N-H...S hydrogen bonds on the formation of thioester in acetyl coenzyme A synthase.

3. Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides.

4. Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture.

5. Nickel-catalyzed reductive carboxylation of styrenes using CO2.

6. Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles.

7. Synthesis of Cyclic Anhydrides via Ligand-Enabled C-H Carbonylation of Simple Aliphatic Acids.

8. Decarbonylative organoboron cross-coupling of esters by nickel catalysis.

9. A facile method for Rh-catalyzed decarbonylative ortho-C-H alkylation of (hetero)arenes with alkyl carboxylic acids.

10. Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides.