Water promoted C-C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC).
A simple and highly efficient synthetic strategy to access 3,3-bipyrrole derivatives by the reaction of dienone derivatives with TosMIC is reported. The reaction involves a van Leusen's pyrrole synthesis followed by an unusual C-C bond cleavage in the presence of water under mild conditions.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China. shunjun@suda.edu.cn.
Rong
R
Wang
Shun-Yi
SY
Wang
Shun-Jun
SJ
Ji
D002244:Carbon / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011758:Pyrroles / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014867:Water / Q000737:chemistry*
D003486:Cyanides; D011758:Pyrroles; D014867:Water; D002244:Carbon; C469613:tosylmethyl isocyanide