Palladium-Catalyzed Decarbonylative Annulation of 2-Arylbenzoic Acids with Internal Alkynes toward Phenanthrenes

Qi Dang; Jiani Chen; Tianbao Li; Long Liu; Tianzeng Huang; Chunya Li; Tieqiao Chen

doi:10.1021/acs.joc.3c01077

Palladium-Catalyzed Decarbonylative Annulation of 2-Arylbenzoic Acids with Internal Alkynes toward Phenanthrenes

J Org Chem. 2023 Sep 1;88(17):12808-12815. doi: 10.1021/acs.joc.3c01077. Epub 2023 Aug 17.

Authors

Qi Dang¹, Jiani Chen¹, Tianbao Li¹, Long Liu¹, Tianzeng Huang¹, Chunya Li¹, Tieqiao Chen¹

Affiliation

¹ Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Laboratory of Fine Chemical, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou 570228, P. R. China.

PMID: 37589566
DOI: 10.1021/acs.joc.3c01077

Abstract

A palladium-catalyzed decarbonylative annulation of 2-arylbenzoic acids with internal alkynes via C(sp²)-H activation has been developed. A series of phenanthrenes were produced in moderate to good yield with good functional group tolerance. The mechanism study indicated that the C(sp²)-H activation should be the rate-determining step during the reaction.