Literature DB >> 16881613

Highly efficient alkylation to ketones and aldimines with Grignard reagents catalyzed by zinc(II) chloride.

Manabu Hatano1, Shinji Suzuki, Kazuaki Ishihara.   

Abstract

A highly efficient alkylation to ketones and aldimines with Grignard reagents in the presence of catalytic trialkylzinc(II) ate complexes derived from ZnCl2 (10 mol %) in situ was developed. This simple Zn(II)-catalyzed alkylation could minimize the well-known but serious problems with the use of only Grignard reagents, which leads to reduction and aldol side products, and the yield of desired alkylation products could be improved.

Entities:  

Year:  2006        PMID: 16881613     DOI: 10.1021/ja0628405

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


  14 in total

1.  Exposing the hidden complexity of stoichiometric and catalytic metathesis reactions by elucidation of Mg-Zn hybrids.

Authors:  Eva Hevia; Jonathan Z Chua; Pablo García-Alvarez; Alan R Kennedy; Matthew D McCall
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-08       Impact factor: 11.205

2.  Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Authors:  Jun Yi; Shorouk O Badir; Rauful Alam; Gary A Molander
Journal:  Org Lett       Date:  2019-05-30       Impact factor: 6.005

3.  Antitumor agents. 272. Structure-activity relationships and in vivo selective anti-breast cancer activity of novel neo-tanshinlactone analogues.

Authors:  Yizhou Dong; Qian Shi; Huei-Chen Pai; Chieh-Yu Peng; Shiow-Lin Pan; Che-Ming Teng; Kyoko Nakagawa-Goto; Donglei Yu; Yi-Nan Liu; Pei-Chi Wu; Kenneth F Bastow; Susan L Morris-Natschke; Arnold Brossi; Jing-Yu Lang; Jennifer L Hsu; Mien-Chie Hung; Eva Y-H P Lee; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2010-03-11       Impact factor: 7.446

4.  Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Timothy J Barker
Journal:  Organometallics       Date:  2018-04-27       Impact factor: 3.876

5.  Accessing Grignard Reluctant Aldehyde in 2-Oxoaldehyde by Organocuprates to Give [1,2] Addition and Oxidative Coupling Reactions.

Authors:  Satyanarayana Battula; Aman A Desai; Jigar Y Soni; Dhruv P Mehta
Journal:  ACS Omega       Date:  2022-02-01

6.  Substituted Aryl Benzylamines as Potent and Selective Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 3.

Authors:  Nigel Vicker; Helen V Bailey; Joanna M Day; Mary F Mahon; Andrew Smith; Helena J Tutill; Atul Purohit; Barry V L Potter
Journal:  Molecules       Date:  2021-11-26       Impact factor: 4.411

7.  Benzylation of Imines with Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Jacob C Hayes; Timothy J Barker
Journal:  European J Org Chem       Date:  2019-01-21

8.  Scalable Synthesis of a Key Intermediate for the Production of Pleuromutilin-Based Antibiotics.

Authors:  Stephen K Murphy; Mingshuo Zeng; Seth B Herzon
Journal:  Org Lett       Date:  2017-08-31       Impact factor: 6.005

9.  Synthesis of 2-Alkenyl-Tethered Anilines.

Authors:  Scott E Denmark; Hyung Min Chi
Journal:  Synthesis (Stuttg)       Date:  2017-05-04       Impact factor: 3.157

10.  Main group multiple C-H/N-H bond activation of a diamine and isolation of a molecular dilithium zincate hydride: experimental and DFT evidence for alkali metal-zinc synergistic effects.

Authors:  Ross Campbell; Daniel Cannon; Pablo García-Álvarez; Alan R Kennedy; Robert E Mulvey; Stuart D Robertson; Jörg Sassmannshausen; Tell Tuttle
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

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