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Rapid Formation of Fluoren‐9‐ones via Palladium‐Catalyzed External Carbon Monoxide‐Free Carbonylation
Author(s) -
Konishi Hideyuki,
Futamata Suguru,
Wang Xi,
Manabe Kei
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800155
Subject(s) - chemistry , carbonylation , carbon monoxide , catalysis , palladium , formate , substrate (aquarium) , oxidative addition , inorganic chemistry , rate determining step , photochemistry , organic chemistry , medicinal chemistry , oceanography , geology
A Pd‐catalyzed carbonylation reaction for the synthesis of fluoren‐9‐ones from 2‐halogenated biphenyls using phenyl formate as a carbon monoxide surrogate was achieved. The combined use of cesium carbonate and o ‐anisic acid resulted in a remarkable rate enhancement, where the reaction was complete within 3 min in some cases. Mechanistic studies indicated that the turnover‐limiting step of the reaction was the C−H bond‐cleaving step or the oxidative addition step, depending on the substrate used.