5452-02-8

Usage

InChI:InChI=1/C12H16O3/c1-4-9(2)15-12(13)10-5-7-11(14-3)8-6-10/h5-9H,4H2,1-3H3

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 78-92-2 iso-butanol 
• 104-93-8 p-methylanizole 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source

Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]

Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes

A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.

Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters

An effective method for alkoxycarbonylation of (hetero)aryl bromides is developed in the presence of in situ-generated phosphinite ligands tBu2POR (R = nBu, nPr, Et or Me). For this purpose commercially available tBu2PCl was used as the pre-ligand in the presence of different alcohols. For the first time cross coupling reactions with two alcohols-one generating the ligand, the other used as substrate-were developed. Through this method, ligand optimization can be performed in a more efficient manner and the desired products could be obtained with good yields and selectivity.

Iron-catalyzed one-pot oxidative esterification of aldehydes

A highly efficient, mild, and simple protocol for Fe(ClO4) 3·xH2O-catalyzed oxidative esterification of aldehydes was developed. Several aromatic and aliphatic aldehydes reacted with simple primary and secondary alcohols, used as the solvent, smoothly in the presence of an iron salt catalyst (10 mol-%) and hydroperoxide (4 equiv.) as an oxidant to generate the corresponding esters in good to excellent yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

PALLADIUM-CATALYZED DOUBLE CARBONYLATION REACTIONS OF ARYL HALIDES AFFORDING α-KETO ESTERS

Various aryl iodides can be converted into α-keto esters in reactions with carbon monoxide and alcohols in the presence of tertiary amines and catalytic amounts of tertiary phosphine-coordinated palladium complexes.