Acid-catalyzed cleavage of C–C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis. Issue 80 (22nd September 2021)

• Record Type: Journal Article
• Authors: Chen, Shaomin; Li, Minghao; Gu, Yanlong
• Is Part Of: Chemical communications. Volume 57:Issue 80(2021)
• Page Start: 10431
• Page End: 10434
• Publication Date: 2021-09-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc04000f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Atropaldehyde acetals acted as masked C2 electrophiles via a novel cleavage of C–C bonds that allowed us to establish novel tandem reactions for the rapid synthesis of 2, 2-disubstituted indolin-3-ones, naphthofurans and stilbenes. 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) SN 2′ 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.