Mild Decarboxylative Activation of Malonic Acid Derivatives by 1,1′-Carbonyldiimidazole

Abstract

Malonic acid derivatives undergo unusually mild decarboxylation when treated with N,N'-carbonyldiimidazole (CDI) at room temperature to generate the carbonyl imidazole moiety in high yield, which can be reacted further with a variety of nucleophiles in an efficient one-pot process.

Solvent- and Catalyst-Free Microwave-Assisted Decarboxylation of Malonic Acid Derivatives

“…The synthesis of carboxylic acid derivatives via malonic ester alkylation, hydrolysis, and subsequent decarboxylation is a well-established method for carboncarbon bond formation [1] [2] [3], and it is one of the most important reactions in organic synthesis. Each of these steps is under constant revision with the aim of developing more efficient procedures in terms of stereocontrol, use of friendly reaction conditions and better yields [4].…”

“…The key step in this multistep reaction sequence is the decarboxylation process, which is usually performed under harsh thermal conditions (up to 200˚C) using conventional [5] [6] or microwave heating [1].…”

“…For example, malonic acid derivatives undergo decarboxylation when treated with N,N'-carbonyldiimidazole (CDI) at room temperature to generate the carbonyl imidazole moiety in high yield [1].…”

Cellulose supported copper nanoparticles as a versatile and efficient catalyst for the protodecarboxylation and oxidative decarboxylation of aromatic acids under microwave heating

“…As a whole, these reactions are high yielding and quite efficient, but they are not free from drawbacks like, the use of expensive or toxic nitrogen/phosphorous containing ligands, high temperature, long reaction time, toxic solvents, strong basic conditions, lack of metal catalyst recyclability etc. In some cases, the free carboxylic acids are required to be converted to esters or anhydrides for effective decarboxylation to take place [13]. Moreover, few examples of decarboxylation at sp 3 -carbon centre are reported [14][15][16].…”

Application of Hydroxyporphyrins-based Phosphite-type Ligands to Asymmetric Pd-Catalyzed Allylic Substitution Reactions

“…[3,32,[44][45][46][47][48][49][50][51] Furthermore, these reactions are the reliable instruments for ligands benchmark testing and the enantiomeric excesses obtained are the simplest scale for evaluating new chiral inductors. [44,50,52] It should also be noted that construction of a quaternary carbon stereocenter via Pdcatalyzed enantioselective synthesis is highly challenging.…”