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A general strategy for the synthesis of highly substituted polycyclic aromatic and heteroaromatic compounds has been developed. The new aromatic annulation is achieved simply by the irradiation of a dichloroethane solution of an acetylene derivative and a vinyl or aryl α-diazo ketone. Mechanistically, the reaction proceeds via the photochemical Wolff rearrangement of the diazo ketone to generate an aryl- or vinylketene, followed by a cascade of three pericyclic reactions. A variety of substituted phenols, naphthalenes, benzofurans, benzothiophenes, indoles, and carbazoles can be prepared by using the method

Detrifluoroacetylative diazo group transfer: (E)-1-diazo-4-phenyl-3-buten-2-one product: (E)-1-diazo-4-phenyl-3-buten-2-one product: α-diazoacetophenone Keywords: acylation; acylation; condensation, ester-active methylene condensation; deacylation; diazo transfer; acetonitrile; assay methods, for butyllithium, with 2-butanol, menthol, 2-pentanol, or 2-propanol, 1,10-phenanthroline indicator; 1,1,1,3,3,3-hexamethyldisilazane; tetrahydrofuran; triethylamine; acetonitrile; diazo compounds; methanesulfonyl azide, shock sensitive

A general strategy for the synthesis of highly substituted polycyclic aromatic and heteroaromatic compounds has been developed. The new aromatic annulation is achieved simply by the irradiation of a dichloroethane solution of an acetylene derivative and a vinyl or aryl α-diazo ketone. Mechanistically, the reaction proceeds via the photochemical Wolff rearrangement of the diazo ketone to generate an aryl- or vinylketene, followed by a cascade of three pericyclic reactions. A variety of substituted phenols, naphthalenes, benzofurans, benzothiophenes, indoles, and carbazoles can be prepared by using the method