Synthesis of Functionalized [3], [4], [5] and [6]Dendralenes through Palladium‐Catalyzed Cross‐Couplings of Substituted Allenoates. (9th December 2016)

• Record Type: Journal Article
• Authors: Lippincott, Daniel J.; Linstadt, Roscoe T. H.; Maser, Michael R.; Lipshutz, Bruce H.
• Is Part Of: Angewandte Chemie. Volume 129:Number 3(2017)
• Page Start: 865
• Page End: 868
• Publication Date: 2016-12-09
• Subjects: Allene -- Dendralene -- Kreuzkupplungen -- Metallorganische Katalyse -- Micellare Katalyse -- Regioselektive Reaktionen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201609636
• Languages: English
• ISSNs: 0044-8249

Abstract

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‐, sp 2 ‐, and sp 3 ‐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. Abstract : Alles aus Allenen : Ein neuer Ansatz zur Synthese von funktionalisierten, symmetrischen und unsymmetrischen [3]‐ bis [6]Dendralenen wird beschrieben. Die Kombination von micellaren Reaktionsbedingungen, niedrigen Katalysatorbeladungen und breitem Substratbereich unterstreicht den schonenden und robusten Charakter der Methode.