Synthesis and cycloaddition reactions of strained alkynes derived from 2,2′-dihydroxy-1,1′-biaryls

Abstract

A series of strained alkynes, based on the 2,2′-dihydroxy-1,1′-biaryl structure, were prepared in a short sequence from readily-available starting materials.

Increasing the versatility of the biphenyl-fused-dioxacyclodecyne class of strained alkynes

“…A report by Xing et al 10 indicated that an effective pairing was a compound containing a methoxy group and a dimethylamino group para - to the ketone and aldehyde enone precursors respectively. Alkyne 15 6 was reacted under basic conditions with 4-dimethylaminobenzaldehyde to give 16 in good yield ( Fig. 3 ).…”

“…We, 5–7 and others, 8 recently reported the synthesis of strained alkynes of general structure 7 , where X/Y = O, NH, NTs, 9 as reagents for copper-free cycloaddition reactions with azides (Fig. 2).…”