Escape from Palladium: Nickel-Catalyzed Catellani Annulation

While Catellani reactions have become increasingly important for arene functionalizations, they have been solely catalyzed by palladium. Here we report the first nickel-catalyzed Catellani-type annulation of aryl triflates and chlorides to form various benzocyclobutene-fused norbornanes in high effi...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 145; no. 20; pp. 11005 - 11011
Main Authors Huo, Jingfeng, Fu, Yue, Tang, Melody J., Liu, Peng, Dong, Guangbin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.05.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
FUNCTIONALIZATION
INTRAMOLECULAR ARYLATION
MECHANISM
REACTIVITY
BOND ACTIVATION
LADDER POLYMERS
PD/NORBORNENE
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Summary:While Catellani reactions have become increasingly important for arene functionalizations, they have been solely catalyzed by palladium. Here we report the first nickel-catalyzed Catellani-type annulation of aryl triflates and chlorides to form various benzocyclobutene-fused norbornanes in high efficiency. Mechanistic studies reveal a surprising outer-sphere concerted metalation/deprotonation pathway during the formation of the nickelacycle, as well as the essential roles of the base and the triflate anion. The reaction shows a broad functional group tolerance and enhanced regioselectivity compared to the corresponding palladium catalysis.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c03780