41848-73-1Relevant academic research and scientific papers
N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes
Ishii, Takuya,Ota, Kenji,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 14073 - 14077 (2019/10/11)
The N-heterocyclic carbene-catalyzed radical relay enables the vicinal alkylacylation of styrenes, acrylates and acrylonitrile using aldehydes and tertiary alkyl carboxylic acid-derived redox-active esters. This protocol introduces tertiary alkyl groups and acyl groups to C-C double bonds with complete regioselectivity to produce functionalized ketone derivatives. The radical relay mechanism involves single electron transfer from the enolate form of a Breslow intermediate and radical addition of the resultant alkyl radical to the alkene followed by radical-radical coupling.
N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Ishii, Takuya,Kakeno, Yuki,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 3854 - 3858 (2019/04/25)
We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.
NBS-promoted rearrangement of 1,1-diarylmethylenecyclopentane
Chang, Meng-Yang,Lin, Chung-Han
, p. 853 - 856 (2012/02/05)
The 1-aroyl-1-aryl-2-bromocyclopentanes 3a, 3b, 3c and 3d (Ar = C 6H5, 2-FC6H4, 3-FC6H 4, 4-FC6H4) were prepared from N-bromosuccinimide (NBS)-promoted rearrangement o
