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Extremely Facile and Selective Nickel‐Catalyzed Allyl Ether Cleavage
Author(s) -
Taniguchi Takahiko,
Ogasawara Kunio
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980504)37:8<1136::aid-anie1136>3.0.co;2-z
Subject(s) - propene , catalysis , nickel , chemistry , cleavage (geology) , ether , medicinal chemistry , propane , organic chemistry , materials science , fracture (geology) , composite material
Child's play! Allyl ethers as protecting groups for hydroxyl functions can be removed readily with a combination of DIBAL and catalytic amounts of [NiCl 2 (dppp)]. Propene is expelled in this remarkably selective reaction, and a nickel‐catalyzed hydroalumination–elimination pathway is proposed [Eq. (a)]. dppp=propane‐1,3‐diylbis(diphenylphosphane).