4994-16-5Relevant articles and documents
Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones
Dong, Guangbin,Xu, Yan,Zhou, Xukai
supporting information, p. 20042 - 20048 (2021/12/03)
The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.
Mechanistic insights into Br?nsted acid-induced nucleophilic substitution of aliphatic imidazole carbamate with halide ions
Saputra, Mirza A.,Forgey, Rashel L.,Henry, Jeffrey L.,Kartika, Rendy
, p. 1392 - 1396 (2015/03/04)
Herein we report interesting reactivity of imidazole carbamate towards nucleophilic substitution with halide ions under Br?nsted acidic conditions. Depending upon reaction conditions, halide ions could readily attack the carboxyl position and trigger decarboxylative alkyl halide formation. Alternatively, halide ions were also found to competitively undergo nucleophilic acyl substitution, which ultimately results in the generation of carbonate dimerization product.
Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins
Wu, Xiaojin,Lu, Yunpeng,Hirao, Hajime,Zhou, Jianrong
supporting information, p. 6014 - 6020 (2013/06/26)
In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright