142256-62-0

Usage

Preparation

Obtained by reaction of pyridinium chlorochromate (PCC) with (2-methoxyphe-–nyl)(2-methyl-phenyl)methanol in the presence of Celite in methylene chloride at r.t. (70%).

InChI:InChI=1/C15H14O2/c1-11-7-3-4-8-12(11)15(16)13-9-5-6-10-14(13)17-2/h3-10H,1-2H3

Upstream product

• 149243-84-5 (2-methoxyphenyl)(2-methylphenyl)methanol 
• 118-90-1 ortho-methylbenzoic acid 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 933-88-0 ortho-toluoyl chloride 
• 135-02-4 ortho-anisaldehyde 
• 95-46-5 2-methylphenyl bromide 
• 130250-61-2 2-methyl-N-methoxy-N-methylbenzamide 
• 31600-86-9 2-methoxyphenyllithium 

Downstream Products

• 154502-72-4 ethyl 2-<2-(2-methoxybenzoyl)phenyl>acetate 
• 154502-75-7 diethyl 2-<2-(2-methoxybenzoyl)phenyl>propanedioate 
• 43217-33-0 9,10-bis(2-methylphenyl)-anthracene 
• 1312211-14-5 C₁₈H₂₀O₂ 
• 93012-14-7 2-<2-(2-methoxybenzoyl)phenyl>acetic acid 

Relevant academic research and scientific papers

Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation

Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.

Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates

Abstract A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)2Cl2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides.

Synthesis of diaryl ketones via a phosphine-free Fukuyama reaction

The synthesis of unsymmetrical diaryl ketones via the Fukuyama coupling of thioesters and organozinc reagents is described. Typically, the synthesis of diaryl ketones using this methodology provides low yields. The simple complex, Pd(dba)2, was found to convert a variety of aryl thioesters to diaryl ketones in good yields. The Royal Society of Chemistry 2011.

Synthesis of sterically hindered ortho-substituted tetraphenylethenes. Electronic effects in the McMurry olefination reaction

Contrary to literature consensus, the McMurry olefination reaction can be extended to the direct synthesis of sterically encumbered tetrakis(2- substituted) tetraphenylethenes from the corresponding 2,2′-disubstituted benzophenones. The reaction exploits

A new synthesis of 3-isochromanone derivatives based on the reaction of o-acylbenzyllithiums with ethyl chloroformate

A new method for the preparation of 3-isochromanone derivatives is reported. The method consists of the ethoxycarbonylation of o-acylbenzyllithiums with ethyl chloroformate and the subsequent NaBH4 reduction of the resulting o-acylphenylacetic