Simple and efficient methods were developed for sp 2-sp 3 and sp 3-sp 3 CC bond-activation reactions of 2-substituted 1,3-diketones. 3-Substituted 3-bromopentane-2,4-diones were deacylated in the presence of an aromatic compound and a silica gel supported Brønsted acid containing sulfonic groups. The carbocation formed by cleavage of the sp 3-sp 3 CC bond of the dione alkylated the aromatic compound.
A novel and efficient method for the activation of the C(sp 3 )-C(sp 3 ) bond was developed. The C(sp 3 )-C(sp 3 ) bond in 3-benzhydryl pentane-2,4-dione was easily cleaved in the presence of NaHSO 4 /SiO 2 to form benzhydryl cation which reacted with aromatic compounds at 110 °C for five to six hours to afford triarylmethanes in good yields. This reaction using Brønsted acids was applicable for the alkylation of electron-rich aromatics containing alkyl halides as a side chain.
Activation of the C-C Bond Using Broensted Acid NaHSO 4/SiO2: Synthesis of Triarylmethanes from 3-Benzhydryl Pentane-2,4-dione and Aromatic Compounds. -(AOYAMA*, T.; HAYAKAWA, M.; OGAWA, S.; NAKAJIMA, E.; MITSUYAMA, E.; IWABUCHI, T.; TAKIDO, T.; KODOMARI, M.; Synlett 25 (2014) 17, 2493-2497, http://dx.
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