Reductive lithiation of alkoxy-substituted benzyl methyl ethers and connection with cross-coupling reactions

Azzena, Ugo; Dettori, Giovanna; Pireddu, Roberta; Pisano, Luisa

doi:10.1016/j.tet.2003.11.085

Cited by 6 publications

(3 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Reaction conditions are similar to (or milder than) those reported for the generation of the same organometallics by previously described deprotonation procedures [39,40], whilst yields were usually better and Barbier-type reaction conditions were not needed.…”

Section: Benzyl Alkyl Ethersmentioning

confidence: 55%

“…More recently, good results were obtained reacting several arylalkyl methyl ethers (31) with an excess of lithium metal and C 10 H 8 (5 mol %) in THF (Scheme 12 and Table 2) [38,39]. The presence of a catalytic amount of C 10 H 8 allowed the high yielding generation of a wide array of benzyllithium derivatives (32), some of which not easily accessible by other methods.…”

Section: Benzyl Alkyl Ethersmentioning

confidence: 99%

See 1 more Smart Citation

Benzylic Organometals via Reductive Metalation Procedures

Azzena¹,

Dettori²,

Pisano

2011

COC

Self Cite

View full text Add to dashboard Cite

The review discusses two different reductive metalation approaches to the generation of benzylic organometals.In the first part, the scope of the generation of polar benzylic organometals by the reductive cleavage of carbon -heteroatom sigma bonds will be presented. Besides briefly showing the evolution of the technique, the review deals with recent achievements in the generation of benzylic derivatives of alkali metals by the reductive cleavage of carbon -halogen, carbon -oxygen, carbon -nitrogen and carbon -sulphur bonds. Significant synthetic applications of this procedure are described, showing that an appropriate choice of reaction conditions (solvent, temperature, alkali metal, employment of an electron shuttle) strongly affects the outcome of the cleavage reaction.In the second part, the application of the reductive metalation to carbon -carbon, carbon -oxygen and carbon -nitrogen double bonds is described, a procedure leading to the generation of vic-diorganometallic derivatives. Synthetic applications of these diorganometals are illustrated, underlining the possible application of 1,2-diarylsubstituted vic-dicarbanions as synthetic analogues of an activated form of an alkali metal that, however, function under homogeneous and mild reaction conditions.

show abstract

Section: Benzyl Alkyl Ethersmentioning

confidence: 55%

Section: Benzyl Alkyl Ethersmentioning

confidence: 99%

Benzylic Organometals via Reductive Metalation Procedures

Azzena¹,

Dettori²,

Pisano

2011

COC

Self Cite

View full text Add to dashboard Cite

show abstract

“…The sixth carbon of benzofuran ring contains free –OH group, which was converted into respective triflate to form methyl 2‐(6‐(((trifluoromethyl)sulfonyl)oxy)‐2,3‐dihydrobenzofuran‐3‐yl)acetate ( Int‐5 ). The Sonogashira Coupling of this triflate with substituted phenyl acetylene was done in presence of palladium and copper catalyst to yield methyl 2‐(6‐(substituted phenylethynyl)‐2,3‐dihydrobenzofuran‐3‐yl)acetates ( Int‐6 a to 6 j ). In the last step, hydrolysis of Int‐6 a to 6 j in weak basic medium forms targeted final molecule as 2‐(6‐(substituted phenylethynyl)‐2,3‐dihydrobenzofuran‐3‐yl)acetic acids (MTS‐201 to 210) .…”

Section: Introductionmentioning

confidence: 99%

Rapid and Efficient Approaches for Synthesis of Some New Aryl Propionic Acid Derivatives and In–Vivo Anti‐Diabetic Screening of Selected Compounds

et al. 2019

View full text Add to dashboard Cite

A series of some new aryl propionic acid derivatives as 2‐(6‐(substituted phenylethynyl)‐2,3‐dihydrobenzofuran‐3‐yl)acetic acids were synthesized. The targeted molecules were prepared by using techniques such as efficient and high‐performance autoclave hydrogenation to reduce highly stable π‐electron system of furan ring and microwave‐assisted rapid Sonogashira Cross‐Coupling reaction between aryl triflate derivatives and substituted aryl acetylenes. The anti‐diabetic screening of selected compounds was performed by using alloxan‐induced diabetic model. The studies include acute and chronic toxicity, effectiveness, change in the behavioral pattern and change in glucose level of the tested animals. The compound 2‐(6‐((4‐ethylphenyl)ethynyl)‐2,3‐dihydrobenzofuran‐3‐yl)acetic acid exhibited maximum anti‐hyperglycemic properties. All the synthesized compounds were characterized by spectroscopic techniques such as 1H‐NMR, 13C‐NMR, IR, Mass spectrometry and single crystal XRD (MTS‐201).

show abstract

Improved and scalable synthesis of building blocks for the modular synthesis of teraryl-based alpha-helix mimetics

Trobe

Breinbauer

2015

Monatsh Chem

View full text Add to dashboard Cite

Reductive lithiation of alkoxy-substituted benzyl methyl ethers and connection with cross-coupling reactions

Cited by 6 publications

References 29 publications

Benzylic Organometals via Reductive Metalation Procedures

Benzylic Organometals via Reductive Metalation Procedures

Rapid and Efficient Approaches for Synthesis of Some New Aryl Propionic Acid Derivatives and In–Vivo Anti‐Diabetic Screening of Selected Compounds

Improved and scalable synthesis of building blocks for the modular synthesis of teraryl-based alpha-helix mimetics

Contact Info

Product

Resources

About