Facile one-pot synthesis of 2,3-dihydro-1H-indolizinium derivatives by rhodium(III)-catalyzed intramolecular oxidative annulation via C-H activation: application to ficuseptine synthesis

作者：Upadhyay Nitinkumar Satyadev; Jayakumar Jayachandran; Cheng Chien Hong

来源：Chemical Communications, 2017, 53(16): 2491-2494.

DOI：10.1039/c7cc00008a

Various substituted indolizidinium, quinolizinium and pyrido[1,2-a]azepinium salts synthesized from benzaldehydes (or alpha,beta-unsaturated aldehydes) and alkyne-amines catalyzed by rhodium complexes via C-H activation are demonstrated. The reaction was carried out under mild reaction conditions using Cu(BF4)(2)center dot 6H(2)O as oxidant and anion source and inexpensive oxygen as a co-oxidant. A reactionmechanism involving imine formation followed by an ortho C-H activation, alkyne insertion and reductive elimination via a 7-membered rhodacycle is proposed. The present method has been successfully applied to the synthesis of a natural product, ficuseptine.

• 出版日期2017
• 单位清华大学