A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles

作者：Zhou, Chengang; Ma, Dawei^*

来源：Chemical Communications, 2014, 50(23): 3085-3088.

DOI：10.1039/c3cc49724k

• REGIOSELECTIVE SYNTHESIS
• GENERAL-SYNTHESIS
• ARYL HYDRAZIDES
• FISCHER
• CYCLOADDITION
• DESIGN
• REARRANGEMENT
• ALKYLATION

CuI-catalyzed coupling of vinyl halides with carbazates gives N-protected N-alkenylhydrazines, which are condensed with ketones under acidic conditions to give polysubstituted pyrroles. The pyrrole synthesis may go through a similar mechanism with Fischer indole synthesis, which involves a [3,3]-sigmatropic rearrangement and other reactions.

• 出版日期2014
• 单位中国科学院; 生命有机化学国家重点实验室; 华东理工大学