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Regioselective Asao-Yamamoto Benzannulations of Diaryl Acetylenes
2014; 16 (22): 5926-5929
Asao-Yamamoto benzannulations transform diarylalkynes into 2,3-diarylnaphthalenes, and regioselective variants of this reaction are of interest for synthesizing substituted polycyclic aromatic systems. It is shown that regioselective cycloadditions occur when one alkyne carbon preferentially stabilizes developing positive charge. Simple calculations of the relative energies of carbocations localized at each alkyne carbon of a substrate predict the regioselectivity, which is not eroded by bulky substituents, including 2,6-disubstituted aryl groups.
View details for DOI 10.1021/ol502938y
View details for Web of Science ID 000345470000026
View details for PubMedID 25383421