title: Synthesis of Functionalized [3], [4], [5] and [6]Dendralenes through Palladium-Catalyzed Cross-Couplings of Substituted Allenoates.
abstract: A mild method for the synthesis of highly functionalized [3]-[6]dendralenes is reported, representing a general strategy to diversely substituted higher homologues of the dendralenes. The methodology utilizes allenoates bearing various substitution patterns, along with a wide range of boron and alkenyl nucleophiles that couple under palladium catalysis leading to sp-, sp2-, and sp3-substituted arrays. Regioselective transformations of the newly formed unsymmetrical dendralene derivatives are demonstrated. The use of micellar catalysis, where water is the global reaction medium, and room temperature reaction conditions, highlights the green nature of this technology.
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA, 93106, USA.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Lippincott
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA, 93106, USA.
authors.forename: Roscoe T H
authors.initials: RT
authors.lastname: Linstadt
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA, 93106, USA.
authors.forename: Michael R
authors.initials: MR
authors.lastname: Maser
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA, 93106, USA.
authors.forename: Bruce H
authors.initials: BH
authors.lastname: Lipshutz
keywords: allenes; cross-couplings; dendralenes; micellar catalysis; organometallic catalysis; regioselective reactions