Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with N-substituted pyrroles.

Autor: Guo J; Department of Chemistry, University of Toronto, Toronto, 80 St. George Street, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca., Cheong O; Department of Chemistry and Biological Chemistry, Nanyang Technological University, 50 Nanyang Avenue, 639798, Singapore., Bamford KL; Department of Chemistry, University of Toronto, Toronto, 80 St. George Street, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca., Zhou J; Department of Chemistry, University of Toronto, Toronto, 80 St. George Street, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca., Stephan DW; Department of Chemistry, University of Toronto, Toronto, 80 St. George Street, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2020 Feb 11; Vol. 56 (12), pp. 1855-1858. Date of Electronic Publication: 2020 Jan 17.
DOI: 10.1039/c9cc08654d
Abstrakt: Metal-free hydroarylation of alkynes with N-substituted pyrroles is shown to be most efficiently mediated by B(C 6 F 5 ) 3 to yield 12 variants of dipyrrole-alkanes, a mono-hydroarylation product and a tetrahydroarylation product of a bis-alkyne. These products were generally obtained in good to excellent yields (up to 95%). Control experiments suggest a mechanism involving FLP addition of the borane and pyrrole to alkyne.
Databáze: MEDLINE
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