Zhang Jiantao, Zhu Weiming, Zhou Peng, Chen Cui, Liu Weibing
College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000, P. R. China.
Chem Commun (Camb). 2023 Aug 1;59(62):9481-9484. doi: 10.1039/d3cc02337k.
A catalyst-free 1,2-difunctionalization of 1,3-dienes with CHCl and TBHP in the presence of NEt to give the dichloromethylhydroxylation products was developed. Various substituents on the aryl ring of the dienes tolerated the reactions and gave the corresponding products in moderate to good yields. When NaCO was employed as the base, the key intermediate α-amino radical could not be formed; therefore, 1,2-peroxyhydroxylation products were obtained instead. This protocol provides an effective and functional group tolerant strategy for diene 1,2-difunctionalization, thus providing great potential for further functionalization and modification of synthetic molecules.
