Catalytic 1,2-dihydronaphthalene and E-aryl-diene synthesis via Co^III-Carbene radical and o-quinodimethane intermediates.

ABSTRACT: Catalytic synthesis of substituted 1,2-dihydronaphthalenes via metalloradical activation of o-styryl N-tosyl hydrazones ((E)-2-(prop-1-en-1-yl)benzene-N-tosyl hydrazones) is presented, taking advantage of the intrinsic reactivity of a cobalt(iii)-carbene radical intermediate. The method has been successfully applied to a broad range of substrates with various R¹ substituents at the aromatic ring, producing the desired ring products in good to excellent isolated yields for substrates with an R² = COOEt substituent at the vinylic position (∼70-90%). Changing the R² moiety from an ester to other substituents has a surprisingly large influence on the (isolated) yields. This behaviour is unexpected for a ra

SUBMITTER: Te Grotenhuis C 

PROVIDER: S-EPMC5857932 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature