Ralf Haiges - Facile synthesis of β-monofluoromethyl alcohols: Nucleophilic monofluoromethylation of aldehydes using TMSCF(SO2Ph)2.

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      Publication Details (including relevant citation   information): Prakash, G. K. Surya, Shao, Nan, Zhang,   Zhe, Ni, Chuanfa, Wang, Fang, Haiges, Ralf, Olah, George A.,   J. Fluorine Chem., 2012, 133,   pp 27-32

      Abstract: α-Fluoromethyl Ph sulfone derivs. have   been extensively employed in various reactions as versatile   fluoromethylating reagents. While nucleophilic   monofluoromethylations of aldehydes have been achieved using   fluoromethyl Ph sulfone or fluorobis(sulfonyl)methanes, a facile   protocol under mild reaction conditions remains an ardently   sought goal. We now report a feasible synthetic approach toward   β-monofluorinated alcs. using   α-trimethylsilyl-α-fluorobis(phenylsulfonyl)methane   [TMSCF(SO2Ph)2, TFBSM] as a novel monofluoromethylating reagent.   Initiated by a catalytic amt. of fluoride, the reagent can be   readily added to a variety of aldehydes providing the desired   products in high yields. Computational and kinetic studies have   revealed the exceptional lability of the Si-C bond in TFBSM   compared with other fluoromethylsilane counterparts. [on   SciFinder(R)]

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