Nickel(0)‐catalyzed hydrocyanation of terminal allenes: a regio‐ and enantioselective approach to branched allylic nitriles
Abstract: A highly branched regioselective nickel(0)-catalyzed hydrocyanation of mono- and 1,1-disubstituted allenes as well as an asymmetric hydrocyanation of 1,1-disubstituted allenes are reported herein, giving access to branched tertiary and quaternary β,γ-allylic nitriles. For the regioselective hydrocyanation of terminal allenes, a nickel(0)/Biphephos catalytic system applicable to a substrate scope containing functional groups such as ester, THP-group, primary aliphatic iodide, and a free carboxylic acid, provides yields up to 96%. By applying a catalytic system of Ni(0)/TADDOL-based bisphosphite catalyst to 1,1-disubstituted allenes, branched quaternary allylic nitriles are obtained in yields up to 99% and enantioselectivities up to 86%. Both protocols take advantage of a manageable HCN source and evidence good atom economy. In addition, the reaction's synthesis utility is highlighted by gram-scale reactions with subsequent assorted transformation of the nitrile group as well as alkylation of the tertiary nitriles in α-position
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Anmerkungen
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Advanced synthesis & catalysis. - 365, 3 (2023) , 335-341, ISSN: 1615-4169
- Ereignis
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Veröffentlichung
- (wo)
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Freiburg
- (wer)
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Universität
- (wann)
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2023
- Urheber
- DOI
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10.1002/adsc.202201189
- URN
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urn:nbn:de:bsz:25-freidok-2341277
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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25.03.2025, 13:50 MEZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Bury, Timm
- Kullmann, Sven
- Breit, Bernhard
- Universität
Entstanden
- 2023
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