Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 29, Pages 9028-9032Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201804788
Keywords
carbonylation; cyclization; heterocycles; palladium; regioselectivity
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Funding
- National Key Research and Development Program of China [2017YFD0200500]
- NSFC [21722202, 21672069, 21472050]
- S&TCSM of Shanghai [18JC1415600]
- Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
- National Program for Support of Top-notch Young Professionals
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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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