Acid-catalyzed cleavage of C–C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis

Abstract

Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) S_N2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon–carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.