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Dehydrogenative Carbon–Carbon Bond Formation Using Alkynyloxy Moieties as Hydrogen‐Accepting Directing Groups
Author(s) -
Minami Yasunori,
Kodama Tatsuro,
Hiyama Tamejiro
Publication year - 2015
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.201505789
Subject(s) - chemistry , catalysis , aryl , hydrogen bond , bond cleavage , acceptor , cleavage (geology) , medicinal chemistry , carbon fibers , rendering (computer graphics) , reinforced carbon–carbon , carbon–hydrogen bond activation , polymer chemistry , photochemistry , organic chemistry , molecule , alkyl , composite number , physics , materials science , computer graphics (images) , fracture (geology) , computer science , composite material , condensed matter physics , geotechnical engineering , engineering
In the presence of a catalyst system consisting of Pd(OAc) 2 , PCy 3 , and Zn(OAc) 2 , the reaction of alkynyl aryl ethers with bicycloalkenes, α,ß‐unsaturated esters, or heteroarenes results in the site‐selective cleavage of two CH bonds followed by the formation of CC bonds. In all cases, the alkynyloxy group acts as a directing group for the activation of an ortho CH bond and as a hydrogen acceptor, thus rendering the use of additives such as an oxidant or base unnecessary.