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Palladium‐Catalyzed 2‐Pyridylmethyl Transfer from 2‐(2‐Pyridyl)ethanol Derivatives to Organic Halides by Chelation‐Assisted Cleavage of Unstrained C sp 3 C sp 3 Bonds
Author(s) -
Niwa Takashi,
Yorimitsu Hideki,
Oshima Koichiro
Publication year - 2007
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/anie.200604472
Subject(s) - chemistry , palladium , moiety , catalysis , chelation , halide , aryl , ethanol , medicinal chemistry , cleavage (geology) , bond cleavage , alcohol , yield (engineering) , organic chemistry , polymer chemistry , alkyl , materials science , fracture (geology) , metallurgy , composite material
Making a break for it : Treatment of 2‐(2‐pyridyl)ethanol derivatives with aryl chlorides in the presence of a palladium catalyst results in the transfer of the pyridylmethyl moiety of the alcohol to yield the corresponding (2‐pyridylmethyl)arene. The reaction proceeds by chelation‐assisted cleavage of an C sp 3C sp 3bond (see scheme) followed by formation of a carbon–carbon bond.