Cleavage and Reassembly CC Bonds of Ynonesto Access Highly Functionalized Ketones
ACS Catalysis(2020)
摘要
An
economical strategy has been designed to formally cleave CC
bonds of ynones through copper-catalyzed carbene chemistry. It proceeds
under mild reaction conditions in a step-economy process by simultaneously
cleaving the CC bonds and constructing C–C bonds. Depending
on the substitution of the ynones, the reactions can proceed efficiently
to generate synthetically useful 1,4-ketoaldehydes and cyclopentenone
compounds. A plausible pathway is proposed that involves an active
cyclopropane intermediate that consequently undergoes a cascade ring-opening
reaction. The method works for a spectrum of ynones and N-tosylhydrazones that give good to excellent yields using a cheap
copper catalytic system.
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关键词
ynones,carbenes,functionalized ketones,cleavage C C bonds,step-economy,synthetic methods
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