The nickel catalyzed regio- and stereoselective condensation of boronic acids to allenamides is documented as a novel synthetic route to stereochemically defined tri-substituted enamides. The protocol has been implemented into a three-component variant intercepting the in situ formed allyl-Ni intermediate with a range of aldehydes. Additionally, evidence for the effective extension of this methodology to Me2Zn is documented. Full rationale on the mechanism as well as its stereochemical outcome is provided by a synergistic experimental/computational approach.
Yang Liu, A.C. (2018). Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study. ORGANIC CHEMISTRY FRONTIERS, 5, 3231-3239 [10.1039/c8qo00729b].
Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study.
Yang LiuMethodology
;Alessandro CerveriMethodology
;Assunta De NisiMethodology
;Magda MonariMethodology
;Marco Bandini
Conceptualization
2018
Abstract
The nickel catalyzed regio- and stereoselective condensation of boronic acids to allenamides is documented as a novel synthetic route to stereochemically defined tri-substituted enamides. The protocol has been implemented into a three-component variant intercepting the in situ formed allyl-Ni intermediate with a range of aldehydes. Additionally, evidence for the effective extension of this methodology to Me2Zn is documented. Full rationale on the mechanism as well as its stereochemical outcome is provided by a synergistic experimental/computational approach.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
