Chemical Science

Direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO (NTs) CH 2 F: the accelerating effect of α-fluorine substitution

X Shen, M Zhou, C Ni, W Zhang, J Hu

Index: Shen, Xiao; Zhou, Min; Ni, Chuanfa; Zhang, Wei; Hu, Jinbo Chemical Science, 2013 , vol. 5, # 1 p. 117 - 122

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Citation Number: 3

Abstract

An efficient and direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO (NTs) CH2F 1 has been developed. In contrast to the previously known detrimental effect of α-fluorine substitution on SN2 reactions, the current monofluoromethylation is accelerated by the α-fluorine substitution. Based on a mechanistic study, a new reactivity of sulfoximine (as a radical monofluoromethylation reagent) is disclosed.