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Formamidines – Versatile Ligands for Zinc‐Catalyzed Hydrosilylation and Iron‐Catalyzed Epoxidation Reactions
Author(s) -
Enthaler Stephan,
Schröder Kristin,
Inoue Shigeyoshi,
Eckhardt Björn,
Junge Kathrin,
Beller Matthias,
Drieß Matthias
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000648
Subject(s) - hydrosilylation , chemistry , chemoselectivity , catalysis , diethylzinc , hydrogen peroxide , zinc , alkyl , aryl , organic chemistry , yield (engineering) , combinatorial chemistry , enantioselective synthesis , materials science , metallurgy
In the present study the abilities of catalysts modified by formamidine ligands have been examined in the zinc‐catalyzed hydrosilylation of ketones and the iron‐catalyzed epoxidation of stilbene. In case of hydrosilylation diethylzinc combined with easily accessible formamidine ligands allow for the efficient reduction of various aryl and alkyl ketones. By using a convenient in situ catalyst system high turnover frequencies up to more than 1.000 h –1 and a broad functional group tolerance were achieved. Moreover, the formamidine ligands were successfully applied in the iron‐catalyzed epoxidation of stilbene with hydrogen peroxide in good yield and chemoselectivity.