Reaction of aliphatic ketones with catechol afforded 2,2-dialkylbenzodioxoles. Treatment of these benzodioxoles with allyltrimethylsilane in the presence of titanium tetrachloride led to 4,4-dialkylhepta-1,6-dienes resulting from a diallylation process. Ring-closing metathesis gave rise to 4,4-dialkylcyclopentenes. (C) 2009 Elsevier Ltd. All rights reserved.
Iron-mediated oxidative C–H coupling of arenes and alkenes directed by sulfur: an expedient route to dihydrobenzofurans
作者:Craig W. Cavanagh、Miles H. Aukland、Quentin Laurent、Alan Hennessy、David J. Procter
DOI:10.1039/c6ob00883f
日期:——
ortho-coupling of arenes and unactivated terminal alkenes mediated by iron, and a palladium-catalysed deallylation/heterocyclisation sequence. The iron-mediated coupling affords linear products of alkene chloroarylation in good yield and with complete regioselectivity. The coupling likely proceeds by redox-activation of the arene partner by iron(III) and alkene addition to the resultant radicalcation.