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.
Nickel catalyzed regio- and stereoselective arylation and methylation of allenamides via coupling reactions. An experimental and computational study / Yang Liu, Alessandro Cerveri, Assunta De Nisi, Magda Monari, Olalla Nieto Faza, Carlos Silva Lopez, Marco Bandini. - In: ORGANIC CHEMISTRY FRONTIERS. - ISSN 2052-4110. - ELETTRONICO. - 5:(2018), pp. 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.
