Activation of alkynes with B(C6F5)3

• Verfasst von: Hansmann, Max M. [VerfasserIn]
• Verfasst von: Melen, Rebecca L. [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Stephan, Douglas W. [VerfasserIn]
• Titel: Activation of alkynes with B(C6F5)3
• Titelzusatz: boron allylation reagents derived from propargyl esters
• Verf.angabe: Max M. Hansmann, Rebecca L. Melen, Frank Rominger, A. Stephen K. Hashmi, and Douglas W. Stephan
• Jahr: 2014
• Jahr des Originals: 2013
• Umfang: 6 S.
• Fussnoten: Im Titel sind die Ziffer "6" "5" "3" tiefgestellt ; Published: December 19, 2013 ; Gesehen am 29.10.2020
• Titel Quelle: Enthalten in: American Chemical SocietyJournal of the American Chemical Society
• Ort Quelle: Washington, DC : American Chemical Society, 1879
• Jahr Quelle: 2014
• Band/Heft Quelle: 136(2014), 2, Seite 777-782
• ISSN Quelle: 1520-5126
• DOI: doi:10.1021/ja4110842
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 173733884X

Abstract

Novel allyl boron compounds are readily synthesized via rearrangement reactions between Lewis acidic B(C6F5)3 and propargyl esters. These reactions proceed through an initial cyclization followed by ring-opening and concurrent C6F5-group migration. In the absence of disubstitution adjacent to the ester oxygen atom, an allyl boron migration rearrangement leads to formal 1,3-carboboration products. These allyl boron compounds act as allylation reagents with aldehydes introducing both a C3-allyl fragment and a C6F5-unit as a single anti-diastereomer. In these reactions, B(C6F5)3 activates the alkynes, prompting the rearrangement processes and enabling installations of C6F5 and R-groups.