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Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu 3 SnOMe
Author(s) -
Komeyama Kimihiro,
Itai Yuuhei,
Takaki Ken
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201601515
Subject(s) - propargyl , catalysis , allylic rearrangement , nickel , chemistry , regioselectivity , palladium , combinatorial chemistry , organic chemistry , polymer chemistry , medicinal chemistry
A practical and scalable nickel‐catalyzed allylic stannylation of allyl acetates with Bu 3 SnOMe is described. A variety of acyclic and cyclic allyl acetates, even with base‐sensitive moieties, undergoes the stannylation by using NiBr 2 /4,4′‐di‐ tert ‐butylbipyridine (dtbpy)/Mn catalyst system to afford highly functionalized allyl stannanes with excellent regioselectivity and yields. Furthermore, the scope of protocol is also extended by the reaction of propargyl acetates, giving rise to propargyl or allenyl stannanes. Additionally, a unique diastereoselectivity using the nickel catalyst different from the palladium was demonstrated for the stannylation of cyclic allyl acetates. In the reaction, inexpensive and stable nickel complexes, abundant reductant (Mn), and atom‐economical stannyl source were used.