Highly regiocontrolled pd-catalyzed cross-coupling reaction of terminal alkynes and allenylphosphine oxides

Michael Rubin, Jelena Markov, Stepan Chuprakov, Donald J. Wink, Vladimir Gevorgyan

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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.

Original languageEnglish (US)
Pages (from-to)6251-6256
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number16
DOIs
StatePublished - Aug 8 2003

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ASJC Scopus subject areas

  • Organic Chemistry

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