A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols

Sweeney, Joseph B. and Ball, Anthony and Lawrence, Philippa and Sinclair, Mackenzie and Smith, Luke (2018) A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols. Angewandte Chemie International Edition, 57 (32). pp. 10202-10206. ISSN 1433-7851

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Abstract

The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad‐scope nickel‐catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron‐deficient amines without the need for glove‐box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron‐deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram‐scale preparation of the calcium antagonist drug substance flunarizine (Sibelium®).

Item Type:
Journal Article
Journal or Publication Title:
Angewandte Chemie International Edition
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1503
Subjects:
ID Code:
126514
Deposited By:
Deposited On:
06 Aug 2019 10:20
Refereed?:
Yes
Published?:
Published
Last Modified:
09 Sep 2020 05:04