Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 41, Pages 14571-14578Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502329
Keywords
allylic compounds; amination; amines; nickel; reaction mechanisms
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Funding
- Scientific Research on Innovative Area Molecular Activation Directed toward Straightforward Synthesis from MEXT [23105546]
- ACT-C from the Japan Science and Technology Agency (JST)
- Frontier Research Base for Global Young Researchers, Osaka University, on the Program of MEXT
- Grants-in-Aid for Scientific Research [26248028] Funding Source: KAKEN
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Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)(2)] and 1,1'-bis(diphenylphosphino)-ferrocene was effectively enhanced by adding nBu(4)NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu(4)NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated eta(3)-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.
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