C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis : Allylation of Ketones by Allylic Alcohols

Wright, Noah and Townsend, Bara and Nicholson, Steven and Robinson, Joshua and Akien, Geoffrey and Ball, Anthony K. and Sweeney, Joseph B. and Doulcet, Julien (2024) C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis : Allylation of Ketones by Allylic Alcohols. Advanced Synthesis & Catalysis, 366 (18). pp. 3833-3838. ISSN 1615-4150

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Abstract

Whilst catalytic ketone allylation using palladium(0) is well–precedented, nickel(0)‐catalysed equivalents of such reactions remain scarce. We report here the first nickel‐catalysed allylation of ketones which uses an easily handled and inexpensive bench‐stable Ni(II) pre‐catalyst. This method avoids generation of stoichiometric by‐products via the use of readily available allyl alcohols, rather than the esters or related derivatives which are often used in such transformations. Under the optimised conditions, 25 monoallylated ketones were obtained in 16% to 98% yield and with high selectivity for the linear (E)–isomers.

Item Type:
Journal Article
Journal or Publication Title:
Advanced Synthesis & Catalysis
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1503
Subjects:
?? allylationc−c couplingketonenickelsustainable catalysiscatalysisorganic chemistry ??
ID Code:
224297
Deposited By:
Deposited On:
24 Sep 2024 10:21
Refereed?:
Yes
Published?:
Published
Last Modified:
09 Oct 2024 14:00