title: Highly regiocontrolled Pd-catalyzed cross-coupling reaction of terminal alkynes and allenylphosphine oxides.
abstract: The cross-coupling of a variety of terminal alkynes 1 with allenylphosphine oxides 2 catalyzed by a Pd(OAc)(2)-TDMPP system provided conjugated endo-enynes 3 solely, while the TCPC-catalyzed reaction of the same regents led to the exclusive formation of exo-isomers 4. The mechanistic rationale for these selective transformations was proposed. Synthetic usefulness of the prepared exo-enyne 4 was demonstrated in the synthesis of multisubstituted diarylbenzylphosphine oxides 5 via the Pd-catalyzed [4+2]-benzannulation reaction.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
authors.forename: Michael
authors.initials: M
authors.lastname: Rubin
authors.forename: Jelena
authors.initials: J
authors.lastname: Markov
authors.forename: Stepan
authors.initials: S
authors.lastname: Chuprakov
authors.forename: Donald J
authors.initials: DJ
authors.lastname: Wink
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan