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Updated: Jan 15, 2026
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium(II) and BF3·OEt2 Cooperatively Catalyzed Regioselective Cyclization of Alkynyl-Tethered Aryl Ethers with
Wang Wang1, Pei-Sen Zou1, Hui-Mei Jiang2
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi), School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Abstract:
Herein, we report palladium(II) and BF3·OEt2 cooperatively catalyzed regioselective ipso-cyclization of alkynyl-tethered para-methoxylated arenes and ortho-cyclization of alkynyl-tethered arenes to prepare spiropyrrolo[2,1-b]quinazolinone-cyclohexadienones and 2,3-fused quinazolinones in good to excellent yields with high regioselectivity, respectively. DFT calculations revealed that the self-assembly of hydrogen-bonding between OAc anion and hydrogen atom of terminal alkyne facilitated ipso-cyclization for the para-methoxy group on the N-aryl moieties. The present method features broad substrate scope, palladacycle as the real catalyst, and hydrogen-bonding enhanced regioselective hydroarylation cyclization.
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