Synthesis of biaryl compounds by vinylogous Michael reactions

Acceptor-substituted cycloalkenones 1 undergo an iron(III)-catalyzed vinylo gous Michael reaction - a sequence of enone-dienol tautomerism, [4+2]-cyclo addition, and retro-aldol reaction - with quinone derivatives 3. A variety of products is obtained ranging from meta-terphenyl precursors 5 to dihydro naphthobenzofurans 7. Reaction of 1,2-naphthoquinone (3e) with vinylogous d onors 1 yields cross-coupled products 12, which can be further converted in to highly functionalized biaryl compounds 13 and 14.