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The First Anti‐Markovnikov Hydration of Terminal Alkynes: Formation of Aldehydes Catalyzed by a Ruthenium( II )/Phosphane Mixture
Author(s) -
Tokunaga Makoto,
Wakatsuki Yasuo
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981102)37:20<2867::aid-anie2867>3.0.co;2-e
Subject(s) - markovnikov's rule , ruthenium , benzenesulfonic acid , chemistry , catalysis , alkyl , sodium salt , salt (chemistry) , medicinal chemistry , sodium , combinatorial chemistry , organic chemistry , inorganic chemistry , regioselectivity
With the right auxiliary phosphane ligands —for example, pentafluorophenyldiphenylphosphane or the sodium salt of 3,3′,3″‐phosphinidynetris(benzenesulfonic acid)—the ruthenium( II )‐catalyzed hydration of terminal alkynes to aldehydes proceeds by the previously unknown anti‐Markovnikov addition of water [Eq. (a)]. Complexes of the type [RuCl 2 (PR 2 R 2 ′ R″) x ] (R=alkyl, Ph) are discussed as catalytically active species.