A general and metal-free radical route to synthesis of 3-acylspiro[4,5]trienones is established that utilizes TBHP (tert-butyl hydrogenperoxide) as an oxidation and a reaction partner to trigger the oxidative ipso-carboacylation of N-arylpropiolamides with aldehydes. This method offers a new difunctionalization of alkynes through oxidative cross coupling of the aldehyde C(sp(2))-H bond with an ipso-aromatic carbon.
A Cu-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes for the synthesis of 3-alkyl spiro[4,5]trienones is described. This method allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-carbocyclization and dearomatization.
An ew metal-free method for the nitrative cyclization of 1-ethynyl-2-(vinyloxy)benzenes with tert-butyl nitrite (t-BuONO), air and water at room temperature is presented, in which an oxygen atom is introduced into the carbon-carbon triple bond to form an ew carbonyl group through dioxygen activation.
We describe a tert-butyl nitrite-catalyzed oxidative
dehydrogenation of hydrazobenzenes for producing azobenzenes. This
method proceeds at ambient temperature and under an atmospheric environment
by employing eco-friendly EtOH as the medium, representing a mild,
general route to the synthesis of various symmetrical and nonsymmetrical
azobenzenes in excellent yields with broad functional group tolerance.
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