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Reductive C−C Coupling from α,β‐Unsaturated Nitriles by Intercepting Keteniminates
dc.contributor.authorHale, Lillian V. A.
dc.contributor.authorSikes, N. Marianne
dc.contributor.authorSzymczak, Nathaniel K.
dc.date.accessioned2019-06-20T17:04:30Z
dc.date.availableWITHHELD_13_MONTHS
dc.date.available2019-06-20T17:04:30Z
dc.date.issued2019-06-17
dc.identifier.citationHale, Lillian V. A.; Sikes, N. Marianne; Szymczak, Nathaniel K. (2019). "Reductive C−C Coupling from α,β‐Unsaturated Nitriles by Intercepting Keteniminates." Angewandte Chemie International Edition 58(25): 8531-8535.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/149503
dc.description.abstractWe present an atom‐economic strategy to catalytically generate and intercept nitrile anion equivalents using hydrogen transfer catalysis. Addition of α,β‐unsaturated nitriles to a pincer‐based Ru−H complex affords structurally characterized κ‐N‐coordinated keteniminates by selective 1,4‐hydride transfer. When generated in situ under catalytic hydrogenation conditions, electrophilic addition to the keteniminate was achieved using anhydrides to provide α‐cyanoacetates in high yields. This work represents a new application of hydrogen transfer catalysis using α,β‐unsaturated nitriles for reductive C−C coupling reactions.An atom‐economic strategy to catalytically generate and intercept nitrile anion equivalents by hydrogen transfer catalysis has been developed. Addition of α,β‐unsaturated nitriles to a pincer‐based Ru−H complex affords keteniminates by selective 1,4‐hydride transfer, which were employed in a net hydrogenative acylation reaction.
dc.publisherWiley-VCH
dc.subject.otherhydrogenative acylation
dc.subject.otherα,β-unsaturated nitriles
dc.subject.otherruthenium
dc.subject.otherreductive C−C coupling
dc.subject.otherketeniminates
dc.titleReductive C−C Coupling from α,β‐Unsaturated Nitriles by Intercepting Keteniminates
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/149503/1/anie201904530.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/149503/2/anie201904530-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/149503/3/anie201904530_am.pdf
dc.identifier.doi10.1002/anie.201904530
dc.identifier.sourceAngewandte Chemie International Edition
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