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

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<mark>Journal publication date</mark>6/08/2018
<mark>Journal</mark>Angewandte Chemie International Edition
Issue number32
Volume57
Number of pages5
Pages (from-to)10202-10206
Publication statusPublished
Early online date12/07/18
Original languageEnglish

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®).