Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 653-657Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.77
Keywords
carbene insertion; copper catalysts; diazoacetates; gold catalysts; naphthalene functionalization; selective insertion
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Funding
- DGI [CTQ2008-00042BQU, CSD2006-0003]
- Junta de Andalucia [P07-FQM-02870]
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The complexes IPrMCl (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene, M = Cu, 1a; M = Au, 1b), in the presence of one equiv of NaBAr'(4) (Ar' = 3,5-bis(trifluoromethyl)phenyl), catalyze the transfer of carbene groups: C(R)CO2Et (R = H, Me) from N2C(R)CO2Et to afford products that depend on the nature of the metal center. The copper-based catalyst yields exclusively a cycloheptatriene derivative from the Buchner reaction, whereas the gold analog affords a mixture of products derived either from the formal insertion of the carbene unit into the aromatic C-H bond or from its addition to a double bond. In addition, no byproducts derived from carbene coupling were observed.
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