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Palladium‐Catalyzed Hydrobenzylation of ortho ‐Tolyl Alkynyl Ethers by Benzylic CH Activation: Remarkable Alkynoxy‐Directing Effect
Author(s) -
Minami Yasunori,
Yamada Kotomi,
Hiyama Tamejiro
Publication year - 2013
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.201304893
Subject(s) - electrophile , palladium , chemistry , catalysis , methylene , medicinal chemistry , surface modification , combinatorial chemistry , organic chemistry
It's selective : The title reaction involves palladium(0)‐catalyzed insertion of CC bonds into benzylic C(sp 3 )H bonds, thus providing efficient access to 2‐methylene‐2,3‐dihydrobenzofurans, which transform into benzofurans upon treatment with a weak acid (e.g., AcOH) and electrophiles. The alkynoxy group serves as a directing group in promoting CH bond functionalization.