» Articles » PMID: 34942056

Mechanochemical Grignard Reactions with Gaseous CO and Sodium Methyl Carbonate

Overview
Specialty Chemistry
Date 2021 Dec 23
PMID 34942056
Citations 13
Authors
Affiliations
Soon will be listed here.
Abstract

A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO ) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.

Citing Articles

Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides.

Zhang X, Hong Y, Zou G Molecules. 2025; 30(5).

PMID: 40076285 PMC: 11901950. DOI: 10.3390/molecules30051060.


Mechanochemical generation of aryl barium nucleophiles from unactivated barium metal.

Kubota K, Kawamura S, Jiang J, Maeda S, Ito H Chem Sci. 2024; .

PMID: 39371463 PMC: 11447672. DOI: 10.1039/d4sc05361c.


Meeting the UN Sustainable Development Goals with Mechanochemistry.

Alic J, Schlegel M, Emmerling F, Stolar T Angew Chem Int Ed Engl. 2024; 63(50):e202414745.

PMID: 39290159 PMC: 11609904. DOI: 10.1002/anie.202414745.


Organomagnesia: Reversibly High Carbon Dioxide Uptake by Magnesium Pyrazolates.

Kracht F, Rolser P, Preisenberger P, Maichle-Mossmer C, Anwander R Adv Sci (Weinh). 2024; 11(32):e2403295.

PMID: 39189457 PMC: 11348227. DOI: 10.1002/advs.202403295.


Mechanochemistry enabling highly efficient Birch reduction using sodium lumps and d-(+)-glucose.

Kondo K, Kubota K, Ito H Chem Sci. 2024; 15(12):4452-4457.

PMID: 38516077 PMC: 10952065. DOI: 10.1039/d3sc06052g.


References
1.
Sawama Y, Yasukawa N, Ban K, Goto R, Niikawa M, Monguchi Y . Stainless Steel-Mediated Hydrogen Generation from Alkanes and Diethyl Ether and Its Application for Arene Reduction. Org Lett. 2018; 20(10):2892-2896. DOI: 10.1021/acs.orglett.8b00931. View

2.
Artz J, Muller T, Thenert K, Kleinekorte J, Meys R, Sternberg A . Sustainable Conversion of Carbon Dioxide: An Integrated Review of Catalysis and Life Cycle Assessment. Chem Rev. 2017; 118(2):434-504. DOI: 10.1021/acs.chemrev.7b00435. View

3.
Piller F, Appukkuttan P, Gavryushin A, Helm M, Knochel P . Convenient preparation of polyfunctional aryl magnesium reagents by a direct magnesium insertion in the presence of LiCl. Angew Chem Int Ed Engl. 2008; 47(36):6802-6. DOI: 10.1002/anie.200801968. View

4.
Beillard A, Bantreil X, Metro T, Martinez J, Lamaty F . Alternative Technologies That Facilitate Access to Discrete Metal Complexes. Chem Rev. 2019; 119(12):7529-7609. DOI: 10.1021/acs.chemrev.8b00479. View

5.
James S, Adams C, Bolm C, Braga D, Collier P, Friscic T . Mechanochemistry: opportunities for new and cleaner synthesis. Chem Soc Rev. 2011; 41(1):413-47. DOI: 10.1039/c1cs15171a. View