Esterification of Alkene with Cerium(IV) Sulfate in Carboxylic Acid

Abstract

Reaction of alkenes [cyclohexene (1), cycloheptene (2), cyclooctene (3), 1-heptene (4), 1-octene (5), styrene (6), 1,7-octadiene (7), indene (8), and 1,2-dihydronaphthalene (9)] with cerium(IV) sulfate (CS) in carboxylic acids [formic acid, acetic acid, and propionic acid] readily yielded the corresponding carboxylic esters. This addition reaction follows the Markovnikov rule. This reaction provides a new simple method for preparing carboxylic esters from alkenes. It was also found that this method is useful for formylation.

Ce(SO4)2-catalysed the highly diastereoselective synthesis of tetrahydroquinolines via an imino Diels Alder ABB′ type reaction and their in vivo toxicity and imaging in zebrafish embryos

“…In addition, this catalyst has been used as a mild and efficient oxidant catalyst for various organic transformations. [21][22][23] In that order, we performed the model reaction in the presence of Ce(SO 4 ) 2 , studying the effect of reducing the catalyst loading from 30 to 15 mol% in MeCN at room temperature, obtaining the desired compound 3a in good to excellent yield, 78-89% (Table 1, entries 3-5).…”

From biodiversity to catalytic diversity: how to control the reaction mechanism by the nature of metallophytes

“…A detailed study of this reaction has been published in various articles by Peterson and co-workers (Peterson 1960;Peterson andAllen 1962, 1963;Peterson and Tao 1964). Thus, the use of different catalysts for that transformation was reported thus far in the literature such as follows: boron trifluoride (Wunderly and Sowa 1937), Pdand Ti(III)-based catalysts (Annby et al 1993;Ferraz and Ribeiro 1992;Larock and Hightower 1993), sulfamic acid (Wang et al 2004), triflic acid (Li et al 2006;Rosenfeld et al 2006), ferric triflate (Choi et al 2008), copper(II) triflate (Taylor et al 2005), indium(III) triflate (Chen and Lu 2007), cerium(IV) sulfate (Horiuchi et al 2003), and ionic liquids (Gu et al 2004). Although these systems effectively catalyze the hydro-acyloxy-addition reaction, they have certain drawbacks such as the use of metals whose reserves will be exhausted in the coming decades, the necessity of handling hazardous reagents and pollutants or the use of non-environmentally friendly solvents and nonreusable catalysts.…”

Cerium (IV) sulfate: A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions

“…Recently cerium (IV) salts have been used for many organic transformations such as the synthesis of carboxylic esters from alkenes [26], synthesis of acetamido phenols [27], conversion of oximes into aldehydes and ketones [28], and one-pot synthesis of 3-acylisoxazoles or polyhydroquinolines [29,30]. The cerium (IV) salts act as Lewis acids in all of these reactions.…”