Direct monofluoromethylation of O-, S-, N-, and P-nucleophiles with PhSO(NTs) CH2F: the accelerating effect of alpha-fluorine substitution

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 a-fluorine substitution on S(N)2 reactions, the current monofluoromethylation is accelerated by the a-fluorine substitution. Based on a mechanistic study, a new reactivity of sulfoximine (as a radical monofluoromethylation reagent) is disclosed.