180624-79-7

Upstream product

• 644-36-0 o-methylphenylacetic acid 
• 75-03-6 ethyl iodide 
• 1587-04-8 1-methyl-2-(2-propenyl)-benzene 

Downstream Products

• 463299-70-9 2-(o-tolyl)but-1-en-1-one 
• 180624-81-1 2-(o-tolyl)butan-1-ol 
• 180624-83-3 1-[1-(2-Methoxy-ethoxymethoxymethyl)-propyl]-2-methyl-benzene 

Relevant academic research and scientific papers

Metal-Free Hydrosilylation of Ketenes with Silicon Electrophiles: Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers

Little-explored hydrosilylation of ketenes promoted by main-group catalysts is reported. The boron Lewis acid tris(pentafluorophenyl)borane accelerates the slow uncatalyzed reaction of ketenes and hydrosilanes, thereby providing a convenient access to the new class of β,β-di- and β-monoaryl-substituted aldehyde-derived silyl enol ethers. Yields are moderate to high, and Z configuration is preferred. The corresponding silyl bis-enol ethers are also available when using dihydrosilanes. The related trityl-cation-initiated hydrosilylation involving self-regeneration of silylium ions is far less effective.

Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes

We describe a photoinduced copper-catalyzed asymmetric radical decarboxylative alkynylation of bench-stable N-hydroxyphthalimide(NHP)-type esters of racemic alkyl carboxylic acids with terminal alkynes, which provides a flexible platform for the construction of chiral C(sp3)?C(sp) bonds. Critical to the success of this process are not only the use of the copper catalyst as a dual photo- and cross-coupling catalyst but also tuning of the NHP-type esters to inhibit the facile homodimerization of the alkyl radical and terminal alkyne, respectively. Owing to the use of stable and easily available NHP-type esters, the reaction features a broader substrate scope compared with reactions using the alkyl halide counterparts, covering (hetero)benzyl-, allyl-, and aminocarbonyl-substituted carboxylic acid derivatives, and (hetero)aryl and alkyl as well as silyl alkynes, thus providing a vital complementary approach to the previously reported method.

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries

A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

Systematic study of chiral discrimination upon crystallisation. Part 2.1 Chiral discrimination of 2-arylalkanoic acids by (1R,2S)-2-amino-1,2-diphenylethanol

The resolution of 2-arylalkanoic acids by (1R,2S)-2-amino-1,2-diphenylethanol has been studied. It has been found that the position of a substituent on the aromatic group of the acids affects resolution efficiency to a considerable extent. Crystal structu