Practical preparation of methyl vinyl ethers through the direct coupling of ketones with CHCl<sub>2</sub>OMe promoted by Mg/TiCl<sub>4</sub>/THF

Ananthan, Bakthavachalam; Yan, Tong

doi:10.1080/00397911.2017.1416635

Cited by 2 publications

(1 citation statement)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Various ketone derivatives were reacted with CHCl 2 OMe in TiCl 4 along with Mg powder in benzene or toluene leads to the product formations in good yields (path II, Scheme 9). [20] …”

Section: Synthesis Of Various Alkyl Enol Ethersmentioning

confidence: 99%

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Ahmad

Jena

Khan

2021

Chemistry An Asian Journal

View full text Add to dashboard Cite

Alkyl enol ethers (AEE) are versatile synthetic intermediates with a unique reactivity pattern. This review article summarizes the synthesis of AEE as well as its reactivity and how enol ether undergoes intermolecular reactions for various bond formation, leading to the construction of several useful organic molecules. The synthetic applications of alkyl enol ethers towards intermolecular bond‐forming reactions include metal‐catalyzed reactions, cycloaddition and heterocycle formation as well as rwactions in the field of natural products synthesis. The achievement of these impressive transformations prove the countless synthetic potential of AEE. The main objective of this review is to bring attentiveness among synthetic chemists to show how AEE extensively can be used to react with both electrophiles as well as nucleophiles, thereby behaving as an ambiphilic reactant. We trust that the unique reactivity pattern of alkyl enol ethers and the fundamental mechanistic idea can attract chemists in AEE chemistry. Exclusively, intermolecular reactions of AEE with other functionalized moieties have not been reviewed to the best of our knowledge.

show abstract

“…Various ketone derivatives were reacted with CHCl 2 OMe in TiCl 4 along with Mg powder in benzene or toluene leads to the product formations in good yields (path II, Scheme 9). [20] …”

Section: Synthesis Of Various Alkyl Enol Ethersmentioning

confidence: 99%

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Ahmad

Jena

Khan

2021

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

A New Entry of Highly Selective and Nucleophilic BrH₂C‐ and ClH₂C‐Titanium Complexes for Carbonyl Coupling

2019

Self Cite

View full text Add to dashboard Cite

The direct coupling of various aldehydes and ketones with CH2Br2 or CH2Cl2 promoted by TiCl4‐Mg bimetallic complex provides an extremely simple, practical, and efficient approach for the construction of bromomethyl or chloromethyl carbinols. The high chemoselectivity of this chemistry is illustrated by the TiCl4‐Mg‐promoted selective coupling of CH2Br2 or CH2Cl2 with an aldehyde in the presence of ketone and selective transfer of CH2Br or CH2Cl to saturated carbonyl moiety. This protocol is also suitable for sterically hindered and enolizable carbonyl compounds.

show abstract

Practical preparation of methyl vinyl ethers through the direct coupling of ketones with CHCl₂OMe promoted by Mg/TiCl₄/THF

Cited by 2 publications

References 15 publications

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

A New Entry of Highly Selective and Nucleophilic BrH₂C‐ and ClH₂C‐Titanium Complexes for Carbonyl Coupling

Contact Info

Product

Resources

About

Practical preparation of methyl vinyl ethers through the direct coupling of ketones with CHCl2OMe promoted by Mg/TiCl4/THF

Cited by 2 publications

References 15 publications

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

A New Entry of Highly Selective and Nucleophilic BrH2C‐ and ClH2C‐Titanium Complexes for Carbonyl Coupling

Contact Info

Product

Resources

About

Practical preparation of methyl vinyl ethers through the direct coupling of ketones with CHCl₂OMe promoted by Mg/TiCl₄/THF

A New Entry of Highly Selective and Nucleophilic BrH₂C‐ and ClH₂C‐Titanium Complexes for Carbonyl Coupling