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Ruthenium‐catalyzed Selective Monoamination of Vicinal Diols
Author(s) -
Bähn Sebastian,
Tillack Annegret,
Imm Sebastian,
Mevius Kathleen,
Michalik Dirk,
Hollmann Dirk,
Neubert Lorenz,
Beller Matthias
Publication year - 2009
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.200900034
Subject(s) - vicinal , ruthenium , ethylene glycol , catalysis , chemistry , pyrrole , diol , organic chemistry , combinatorial chemistry
Highly selective monoamination of vicinal diols : The reaction of vicinal diols with primary and secondary amines is catalyzed by [Ru 3 (CO) 12 ] and N ‐phenyl‐2‐(dicyclohexyl‐phosphanyl)pyrrole to generate the corresponding amino alcohols with high selectivity and good yields.The monoamination of vicinal diols in the presence of in situ generated ruthenium catalysts has been investigated. Among the various phosphines tested in combination with [Ru 3 (CO) 12 ], N ‐phenyl‐2‐(dicyclohexyl‐phosphanyl)pyrrole showed the best performance. After optimization of the reaction conditions this system was applied to different secondary amines and anilines as well as a number of vicinal diols. With the exception of ethylene glycol, monoamination of the vicinal diols occurred selectively and the corresponding amino alcohols were obtained in good yields, producing water as the only side product.