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Literature DB >> 29191023

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

Amira H Dardir¹, Patrick R Melvin¹, Ryan M Davis¹, Nilay Hazari¹, Megan Mohadjer Beromi¹.

Abstract

Esters are valuable electrophiles for cross-coupling due to their ubiquity and ease of synthesis. However, harsh conditions are traditionally required for the effective cross-coupling of ester substrates. Utilizing a recently discovered precatalyst, Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of the C(acyl)-O bond of aryl esters that proceed under mild conditions are reported. The Pd(II) precatalyst is highly active because it is reduced to the Pd(0) active species more rapidly than previous precatalysts.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2017 PMID： 29191023 PMCID： PMC5786428 DOI： 10.1021/acs.joc.7b02588

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

48 in total

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Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

2. Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors: Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal: Angew Chem Int Ed Engl Date: 2012-05-09 Impact factor: 15.336

Review 3. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Authors: Javier Magano; Joshua R Dunetz
Journal: Chem Rev Date: 2011-03-09 Impact factor: 60.622

4. 4-Fluoro and 4-Hydroxy Pyrrolidine-thioxotetrahydropyrimidinones: Organocatalysts for Green Asymmetric Transformations in Brine.

Authors: Nikolaos Kaplaneris; Giorgos Koutoulogenis; Marianna Raftopoulou; Christoforos G Kokotos
Journal: J Org Chem Date: 2015-05-11 Impact factor: 4.354

5. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors: Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

6. Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species.

Authors: Chien-Tien Chen; Jen-Huang Kuo; Vijay D Pawar; Yogesh S Munot; Shieu-Shien Weng; Cheng-Hsiu Ku; Cheng-Yuan Liu
Journal: J Org Chem Date: 2005-02-18 Impact factor: 4.354

7. Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids.

Authors: Kei Muto; Taito Hatakeyama; Kenichiro Itami; Junichiro Yamaguchi
Journal: Org Lett Date: 2016-09-27 Impact factor: 6.005

8. Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

Authors: Mamoru Tobisu; Toshiaki Shimasaki; Naoto Chatani
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

9. Cross-coupling reactions of aryl pivalates with boronic acids.

Authors: Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal: J Am Chem Soc Date: 2008-10-08 Impact factor: 15.419

10. Copper-Catalyzed sp(3) C-H Aminative Cyclization of 2-Alkyl-N-arylbenzamides: An Approach for the Synthesis of N-Aryl-isoindolinones.

Authors: Kanako Nozawa-Kumada; Jun Kadokawa; Takehiro Kameyama; Yoshinori Kondo
Journal: Org Lett Date: 2015-09-08 Impact factor: 6.005

12 in total

1. Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.

Authors: Amira H Dardir; Nilay Hazari; Scott J Miller; Christopher R Shugrue
Journal: Org Lett Date: 2019-07-10 Impact factor: 6.005

2. 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

3. Differences in the Performance of Allyl Based Palladium Precatalysts for Suzuki-Miyaura Reactions.

Authors: Matthew R Espinosa; Angelino Doppiu; Nilay Hazari
Journal: Adv Synth Catal Date: 2020-08-27 Impact factor: 5.837

4. Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

Authors: Timothy B Boit; Nicholas A Weires; Junyong Kim; Neil K Garg
Journal: ACS Catal Date: 2017-12-20 Impact factor: 13.084

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

Authors: Amira H Dardir; Irene Casademont-Reig; David Balcells; Jonathan D Ellefsen; Matthew R Espinosa; Nilay Hazari; Nicholas E Smith
Journal: Organometallics Date: 2021-05-27 Impact factor: 3.837

6. Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors: Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal: Angew Chem Int Ed Engl Date: 2020-06-05 Impact factor: 15.336

10. Suzuki-Miyaura Cross-Coupling of Esters by Selective O-C(O) Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]₂ Precatalysts: Catalyst Evaluation and Mechanism.

Authors: Shiyi Yang; Tongliang Zhou; Albert Poater; Luigi Cavallo; Steven P Nolan; Michal Szostak
Journal: Catal Sci Technol Date: 2021-03-25 Impact factor: 6.119