Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C=C Double Bonds.
Several phosphonium and ammonium triarylborohydrides, which are intermediates in hydrogenation reactions catalyzed by frustrated Lewis pairs, were synthesized in high yield under mild conditions from triaryl boranes, ammonium or phosphonium halides, and triethylsilane. The kinetics and mechanisms of the reactions of these hydridoborate salts with benzhydrylium ions, iminium ions, quinone methides, and Michael acceptors were investigated, and their nucleophilicity was determined and compared with that of other hydride donors.
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München (Germany) http://www.cup.uni-muenchen.de/oc/mayr/
Varvara
V
Morozova
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München (Germany) http://www.cup.uni-muenchen.de/oc/mayr/
Peter
P
Mayer
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, 81377 München (Germany) http://www.cup.uni-muenchen.de/oc/mayr/. guillaume.berionni@cup.uni-muenchen.de.
Guillaume
G
Berionni
frustrated Lewis pairs; hydride donors; kinetics; nucleophilicity; reaction mechanisms