Trifluoromethyl ketones were found to be coupled with arynes in three modes depending upon their substitution patterns, namely C-C bond cleavage, [2+2] cycloaddition and O-arylation.
Aryne Reaction with Trifluoromethyl Ketones in Three Modes: C-C Bond Cleavage, [2 + 2] Cycloaddition and O-Arylation. -It is demonstrated that benzyl trifluoromethyl ketones (II) serve as versatile substrates for a C-C bond cleavage reaction. The reaction mode can distinctly be switched into [2 + 2] cycloaddition or O-arylation depending on the substitution pattern, resulting in stereoselective formation of a benzocyclobutenol (IX) or an enol ether (VII). -(YOSHIDA*, H.; ITO, Y.; YOSHIKAWA, Y.; OHSHITA, J.; TAKAKI, K.; Chem. Commun. (Cambridge) 47 (2011) 30, 8664-8666, http://dx.doi.org/10.1039/c1cc12820e ; Dep. Appl. Chem., Fac. Eng., Hiroshima Univ., Higashi-Hiroshima 739, Japan; Eng.) -M. Paetzel 49-083
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