3 years ago

Palladium-Catalyzed C–H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes

Palladium-Catalyzed C–H Bond Functionalization of 6,6-Diphenylfulvenes: An Easier Access to C1-Arylated and C1,C4-Diarylated Fulvenes
Hamed Ben Ammar, Henri Doucet, Jean-François Soulé, Vincent Dorcet, Mariem Brahim
Conditions allowing the palladium-catalyzed regioselective direct arylation of fulvene derivatives are reported. The nature of the aryl source exhibits an important influence on the yield. The reaction of fulvenes with aryl bromides gave poor yields, whereas the use of benzenesulfonyl chlorides gave rise to fulvenes arylated at C1- and C4-positions on the 5-membered ring in good yields. The reaction tolerates various substituents such as nitrile, nitro, fluoro, trifluoromethyl, chloro, or even bromo on the benzenesulfonyl chloride.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00900

DOI: 10.1021/acs.orglett.7b00900

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