20881-29-2Relevant articles and documents
N-Heterocyclic Carbene Catalyzed γ-Dihalomethylenation of Enals by Single-Electron Transfer
Yang, Wen,Hu, Weimin,Dong, Xiuqin,Li, Xin,Sun, Jianwei
, p. 15783 - 15786 (2016)
An N-heterocyclic carbene (NHC) catalyzed dihalomethylenation of enals is described. It is a rare example of merging NHC catalysis with single-electron chemistry, a challenging topic with limited previous success. The versatile carbon-centered trihalomethyl radicals have been demonstrated, for the first time, to be compatible with an NHC-bound intermediate, thus leading to efficient and regioselective intermolecular C?C bond formation. The mild process provides straightforward access to unsaturated δ,δ-dihalo esters.
Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
Yoo, Jae Won,Seo, Youngran,Park, Jong Beom,Kim, Young Gyu
, (2020/01/13)
Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
A metal-free desulfurizing radical reductive C-C coupling of thiols and alkenes
Qin, Qixue,Wang, Weijing,Zhang, Cheng,Song, Song,Jiao, Ning
supporting information, p. 10583 - 10586 (2019/09/06)
An intermolecular reductive C-C coupling of electrophilic alkyl radicals and alkenes has been developed. Thiols were used as both hydrogen-donating reagents and alkyl radical precursors in the presence of triethyl phosphite and radical initiator. A wide range of alkenes, including styrenes, and aliphatic olefins were well tolerated in this transformation. Mechanistic studies indicated that a phosphite promoted radical desulfurization of thiols to access electrophilic alkyl radicals and a radical chain propagation process may be involved in this transformation.