139313-45-4Relevant articles and documents
Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination
Kakiuchi, Fumitoshi,Kochi, Takuya,Kumagai, Takaaki,Muto, Kazuma
, p. 24500 - 24504 (2021/10/19)
Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.
Allylsamarium bromide-mediated cascade cyclization of homoallylic esters. Synthesis of 2-(2-hydroxyalkyl)cyclopropanols and 2-(2-hydroxyethyl)bicyclo[2.1.1]hexan-1-ols
Shen, Mengmeng,Tu, Yawei,Xie, Guanqun,Niu, Qingsheng,Mao, Hui,Xie, Tingting,Flowers, Robert A.,Lv, Xin,Wang, Xiaoxia
, p. 52 - 61 (2016/09/12)
In continuation of our previous study on the intramolecular reductive coupling of simple homoallylic esters promoted by allylSmBr/HMPA/H2O, which afforded a facile synthesis of 2-(2-hydroxyalkyl)cyclopropanols, here we report the reductive casc
Cobalt(II) Chloride Catalyzed Acylation of Alcohols with Acetic Anhydride: Scope and Mechanism
Iqbal, Javed,Srivastava, Rajiv Ranjan
, p. 2001 - 2007 (2007/10/02)
Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield.Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones.Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate.The β-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting β-acetoxy carbonyl compound is observed.A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene.A mechanism for these acylations is proposed by invoking an electron-transfer process.