Ligand-Controlled Palladium(II)-Catalyzed Regiodivergent Carbonylation of Alkynes: Syntheses of Indolo[3,2-c]coumarins and Benzofuro[3,2-c]quinolinones

Angewandte Chemie
Dong DingXuefeng Jiang

Abstract

Regiodivergent syntheses of indolo[3,2-c]coumarins and benzofuro[3,2-c]quinolinones through a controllable palladium(II)-catalyzed carbonylative cyclization are established. The chemo- and regioselectivity are exclusively tuned by the ligand on the palladium catalyst. The rigid framework of the electron-deficient ligand promotes the O-attack/N-carbonylation cyclization leading to benzofuro[3,2-c]quinolinones, while a sterically bulky and electron-rich ligand facilitates N-attack/O-carbonylation cyclization to generate indolo[3,2-c]coumarins. Furthermore, various other nucleophiles are applicable for delivering a variety of indoloquinolinones, pyranoquinolones, and chromeno[3,4-c]quinolinones in one step, and serves as a method for creating compound libraries for drug discovery.

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Citations

Jun 25, 2019·Chemical Communications : Chem Comm·Jitan ZhangMeihua Xie
Feb 14, 2020·Chemical Communications : Chem Comm·Linwei ZengSunliang Cui
Sep 25, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jian-Biao LiuDe-Zhan Chen
Feb 9, 2021·Organic Letters·Kai Liu, Xuefeng Jiang
Nov 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wan Pyo HongHee Nam Lim
Nov 7, 2020·Journal of the American Chemical Society·Stephen J TereniakShannon S Stahl
Dec 12, 2019·The Journal of Organic Chemistry·V P Rama Kishore PuttaChandi C Malakar
Sep 8, 2021·Chemistry : a European Journal·Genesis Infante, Sara Eisler
Dec 7, 2021·Journal of the American Chemical Society·Leiyang BaiXuefeng Jiang

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