Frustrated Lewis Pair Mediated 1,2‐Hydrocarbation of Alkynes

Abstract: Frustrated Lewis pair (FLP) chemistry enables a rare example of alkyne 1,2‐hydrocarbation with N‐methylacridinium salts as the carbon Lewis acid. This 1,2‐hydrocarbation process does not proceed through a concerted mechanism as in alkyne syn‐hydroboration, or through an intramolecular 1,3‐hydride migration as operates in the only other reported alkyne 1,2‐hydrocarbation reaction. Instead, in this study, alkyne 1,2‐hydrocarbation proceeds by a novel mechanism involving alkyne dehydrocarbation with a carbon Lewis acid based FLP to form the new C−C bond. Subsequently, intermolecular hydride transfer occurs, with the Lewis acid component of the FLP acting as a hydride shuttle that enables alkyne 1,2‐hydrocarbation.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Frustrated Lewis Pair Mediated 1,2‐Hydrocarbation of Alkynes ; volume:129 ; number:31 ; year:2017 ; pages:9330-9334 ; extent:5 ; Angewandte Chemie ; 129, Heft 31 (2017), 9330-9334 (gesamt 5)

Contributors, Places and Time

• Creator: Fasano, Valerio ; Curless, Liam D. ; Radcliffe, James E. ; Ingleson, Michael J.

Further information

• DOI: 10.1002/ange.201705100
• URN: urn:nbn:de:101:1-2022091506084164932282
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:32 AM CEST