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

Honggui Lv; Xinyue Xu; Jing Li; Xiaobo Huang; Guoyong Fang; Lifei Zheng

doi:10.1002/anie.202206420

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

Angew Chem Int Ed Engl. 2022 Aug 22;61(34):e202206420. doi: 10.1002/anie.202206420. Epub 2022 Jul 11.

Authors

Honggui Lv^{1

2}, Xinyue Xu^{1

3}, Jing Li³, Xiaobo Huang³, Guoyong Fang³, Lifei Zheng^{1

2}

Affiliations

¹ Wenzhou Institute, University of Chinese Academy of Sciences, Wenzhou, 325001, China.
² Oujiang Laboratory of ZheJiang Lab for Regenerative Medicine, Vision and Brain Health, Wenzhou, 325001, China.
³ Wenzhou University, College of Chemistry and Materials Engineering, Wenzhou, 325035, China.

PMID: 35764532
DOI: 10.1002/anie.202206420

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 Cu^II precatalyst and piezoelectric materials. The highly polarized BaTiO₃ or PbTiO₃ under mechanical agitation can act as an electron donor to realize the recycling of Cu^II and Cu^I . Control experiments and density functional theory calculations have been performed to support the proposed mechanistic rationale for the cascade reactions.

Keywords: Ball Milling; Copper Catalysis; Mechanochemistry; Piezoelectric Materials; Radical Reaction.

Abstract

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