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Room Temperature Decarboxylative and Oxidative [2+2+2] Annulation of Benzoic Acids with Alkynes Catalyzed by an Electron‐Deficient Rhodium(III) Complex
Author(s) -
Honjo Yusaku,
Shibata Yu,
Kudo Eiji,
Namba Tomoya,
Masutomi Koji,
Tanaka Ken
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703928
Subject(s) - rhodium , annulation , chemistry , catalysis , decarboxylation , oxidative decarboxylation , medicinal chemistry , decarbonylation , cyclopentadienyl complex , bond cleavage , oxidative phosphorylation , solvent , photochemistry , stereochemistry , organic chemistry , biochemistry
It has been established that an electron‐deficient (η 5 ‐cyclopentadienyl)rhodium(III) [Cp E Rh III ] complex is capable of catalyzing the decarboxylative and oxidative [2+2+2] annulation of benzoic acids with alkynes to produce substituted naphthalenes at room temperature. The appropriate choice of the additive and the solvent is crucial for this transformation. This catalyst system allowed use of oxygen as a terminal oxidant and broadened the substrate scope including both aromatic and aliphatic alkynes. In this catalysis, the electron deficient nature of the Cp E Rh III catalyst would cause the strong rhodium‐π interaction, which accelerates the decarboxylation as well as the C−H bond cleavage.