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Literature DB >> 25650559

Nickel-catalyzed enantioselective C-C bond formation through C(sp2)-O cleavage in aryl esters.

Josep Cornella¹, Evan P Jackson, Ruben Martin.

Abstract

We report the first enantioselective CC bond formation through CO bond cleavage using aryl ester counterparts. This method is characterized by its wide substrate scope and results in the formation of quaternary stereogenic centers with high yields and asymmetric induction.

Entities: Chemical Gene

Keywords: C-O cleavage; C-O electrophiles; aryl esters; nickel catalysis

Year: 2015 PMID： 25650559 DOI： 10.1002/anie.201412051

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

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Cited

10 in total

1. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors: Louis-Charles Campeau; Nilay Hazari
Journal: Organometallics Date: 2018-11-27 Impact factor: 3.876

2. Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors: Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal: J Am Chem Soc Date: 2017-09-07 Impact factor: 15.419

Nickel-catalyzed enantioselective C-C bond formation through C(sp2)-O cleavage in aryl esters.

1. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

2. Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

3. Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.

4. Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst.

5. Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters.

6. Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp³)-H bonds.

7. Total synthesis of cyrneines A-B and glaucopine C.

8. Efficient cleavage of aryl ether C-O linkages by Rh-Ni and Ru-Ni nanoscale catalysts operating in water.

9. Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester via chemoselective C(acyl)-O bond activation.

10. Computational Analysis of Enantioselective Pd-Catalyzed α-Arylation of Ketones.