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Ruthenium‐Catalyzed trans ‐Selective Hydrostannation of Alkynes
Author(s) -
Rummelt Stephan M.,
Fürstner Alois
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201311080
Subject(s) - regioselectivity , catalysis , ruthenium , chemistry , selectivity , lewis acids and bases , substrate (aquarium) , transition metal , combinatorial chemistry , organic chemistry , oceanography , geology
In contrast to all other transition‐metal‐catalyzed hydrostannation reactions documented in the literature, the addition of Bu 3 SnH across various types of alkynes proceeds with excellent trans selectivity, provided the reaction is catalyzed by [Cp*Ru]‐based complexes. This method is distinguished by a broad substrate scope and a remarkable compatibility with functional groups, including various substituents that would neither survive under the conditions of established Lewis acid mediated trans hydrostannations nor withstand free‐radical reactions. In case of unsymmetrical alkynes, a cooperative effect between the proper catalyst and protic functionality in the substrate allows outstanding levels of regioselectivity to be secured as well.