Mechanochemical Divergent Syntheses of Oxindoles and α‐Arylacylamides via Controllable Construction of C−C and C−N Bonds by Copper and Piezoelectric Materials

Abstract

Herein, we present the divergent syntheses of α‐arylacylamides and oxindoles via mechanoredox chemistry by using easily accessible α‐bromo N‐sulfonyl amides as starting materials. Our system consists of a catalytic amount of CuII precatalyst and piezoelectric materials. The highly polarized BaTiO3 or PbTiO3 under mechanical agitation can act as an electron donor to realize the recycling of CuII and CuI. Control experiments and density functional theory calculations have been performed to support the proposed mechanistic rationale for the cascade reactions.

Electron/hole piezocatalysis in chemical reactions

“…Then, the radical intermediate Finally, the final product (d) was achieved after deprotonation of (c). Lv et al (2022) 214 presented, for the first time, a highly regioselective divergent synthesis of a-arylacylamides over BaTiO 3 (3 mm) with a yield of 45-89% and oxindoles over PbTiO 3 (2 mm) with a yield of 71-92% in the presence of the Cu(II) precatalyst under BM agitation (30 Hz) (Fig. 12A).…”