79676-71-4Relevant academic research and scientific papers
Ortho-lithiation reaction of aryl triflones
Sumii, Yuji,Taniguchi, Misaki,Xu, Xiu-Hua,Tokunaga, Etsuko,Shibata, Norio
, p. 5635 - 5641 (2018)
The ortho-lithiation of substituted arenes is a powerful methodology to synthesize ortho-substituted arenes. While a wide variety of directed metalation groups (DMGs) have been reported, trifluoromethyl sulfone has never been used. We disclose the first example of ortho-lithiation of aryl triflones. We found that the trifluoromethyl sulfonyl group is not only an important structural motif in biologically active molecules and specialty materials, but also an excellent DMG moiety for ortho-metalation reactions. The use of a base that causes steric hindrance, LTMP, is the key for successful transformation to furnish a variety of ortho-substituted aryl triflones in good yields. Further functionalization of resulting ortho-substituted aryl triflones was demonstrated by metal-catalyzed coupling reactions.
