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Catalytic 1,4‐Rhodium(III) Migration Enables 1,3‐Enynes to Function as One‐Carbon Oxidative Annulation Partners in CH Functionalizations
Author(s) -
Burns David J.,
Lam Hon Wai
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406072
Subject(s) - rhodium , annulation , allylic rearrangement , alkyne , chemistry , catalysis , carbon fibers , oxidative phosphorylation , stereochemistry , function (biology) , combinatorial chemistry , organic chemistry , materials science , biology , biochemistry , evolutionary biology , composite number , composite material
1,3‐Enynes containing allylic hydrogens cis to the alkyne are shown to act as one‐carbon partners, rather than two‐carbon partners, in various rhodium‐catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double CH activation, involving a hitherto rare example of the 1,4‐migration of a Rh III species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.