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Testing Phosphanes in the Palladium Catalysed Allylation of Secondary and Primary Amines
Author(s) -
Thoumazet Claire,
Grützmacher Hansjörg,
Deschamps Bernard,
Ricard Louis,
le Floch Pascal
Publication year - 2006
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200600592
Subject(s) - chemistry , aniline , denticity , palladium , catalysis , ligand (biochemistry) , allylic rearrangement , acceptor , primary (astronomy) , combinatorial chemistry , organic chemistry , crystal structure , biochemistry , physics , receptor , astronomy , condensed matter physics
The electronic nature of the ligand plays a crucial role in the palladium‐catalysed allylation of amines with allylic alcohols. The better the ligand is as a π acceptor, the more active the catalyst. Experiments with a series with mono‐ and bidentate ligands featuring phosphanes and phospholes applied in the catalytic allylation of aniline clearly demonstrate this. Bolstered by DFT calculations, we have devised a new efficient catalyst for this process which carries the strong π acceptor 1,2,5‐triphenylphosphole as a ligand. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)