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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505789
Subject(s) - chemistry , catalysis , aryl , hydrogen bond , acceptor , bond cleavage , medicinal chemistry , rendering (computer graphics) , carbon fibers , cleavage (geology) , carbon–hydrogen bond activation , reinforced carbon–carbon , hydrogen , polymer chemistry , organic chemistry , photochemistry , molecule , alkyl , composite number , materials science , physics , computer graphics (images) , fracture (geology) , computer science , composite material , condensed matter physics
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.