The propargyl rearrangement to functionalised allyl-boron and borocation compounds

• Verfasst von: Wilkins, Lewis C. [VerfasserIn]
• Verfasst von: Wieneke, Philipp [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Hansmann, Max M. [VerfasserIn]
• Titel: The propargyl rearrangement to functionalised allyl-boron and borocation compounds
• Verf.angabe: Lewis C. Wilkins, James R. Lawson, Philipp Wieneke, Frank Rominger, A. Stephen K. Hashmi, Max M. Hansmann, and Rebecca L. Melen
• Umfang: 7 S.
• Fussnoten: Gesehen am 25.08.2017
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Jahr Quelle: 2016
• Band/Heft Quelle: 22(2016), 41, S. 14618-14624
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201602719
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1562740849

Abstract

A diverse range of Lewis acidic alkyl, vinyl and aryl boranes and borenium compounds that are capable of new carbon-carbon bond formation through selective migratory group transfer have been synthesised. Utilising a series of heteroleptic boranes [PhB(C6F5)2 (1), PhCH2CH2B(C6F5)2 (2), and E-B(C6F5)2(C6F5)C=C(I)R (R=Ph 3 a, nBu 3 b)] and borenium cations [phenylquinolatoborenium cation ([QOBPh][AlCl4], 4)], it has been shown that these boron-based compounds are capable of producing novel allyl- boron and boronium compounds through complex rearrangement reactions with various propargyl esters and carbamates. These reactions yield highly functionalised, synthetically useful boron substituted organic compounds with substantial molecular complexity in a one-pot reaction.