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Nickel‐Catalysed Bis‐Allylation of Activated Nucleophiles with Allyl Alcohol
Author(s) -
Blieck Rémi,
Azizi Mohamed Salah,
Mifleur Alexis,
Roger Maxime,
Persyn Clément,
Sauthier Mathieu,
Bonin Hélène
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501556
Subject(s) - chemistry , nucleophile , nickel , allylic rearrangement , catalysis , alcohol , allylic alcohol , organic chemistry , combinatorial chemistry , medicinal chemistry
Nickel‐based catalysis allows the efficient bis‐allylation of soft nucleophiles with allylic alcohols. The reaction is best promoted by a combination of Ni(cod) 2 (cod = cyclooctadienyl) and diphenylphosphinobutane under additive‐free conditions. Alternatively, nickel(II) precursors can be used provided that a reductant is used to generate the nickel(0) species. The NiCl 2 /Zn combination is particularly simple, and can advantageously replace the use of the more air‐sensitive Ni(cod) 2 precursor. The scope of the reaction was studied with nucleophiles and allylic derivatives suitable for bis‐allylation reactions.