Abstract
The first metal free selective C-F bond activation of a CF(3) group was observed with N-heterocyclic silylenes [PhC(NtBu)(2)SiCl] (1) and [CH{(C=CH(2))(CMe)(2,6-iPr(2)C(6)H(3)N)(2)}Si] (2) with PhN=C(CF(3))(2). The reaction proceeds in a 1 : 1 molar ratio to yield the mono C-F bond activated products 3 and 4 with each containing a CF(2) group. Both the reactions proceed through an unprecedented selective activation of one of the C-F bonds rather than forming the [1+2] cycloaddition product containing the three-membered SiNC rings.
Highlights
The first metal free selective C–F bond activation of a CF3 group was observed with N-heterocyclic silylenes [PhC(NtBu)2SiCl] (1) and [CH{(CQCH2)(CMe)(2,6-iPr2C6H3N)2}Si] (2) with PhNQC(CF3)[2]
The reaction proceeds in a 1 : 1 molar ratio to yield the mono C–F bond activated products 3 and 4 with each containing a CF2 group. Both the reactions proceed through an unprecedented selective activation of one of the C–F bonds rather than forming the [1+2] cycloaddition product containing the three-membered SiNC rings
Bifluorinated organic compounds such as 1,1-difluoro-1alkenes find increasing application in chemical, material and biological processes because of their unique activity.[1]. These bifluorinated compounds are generally prepared by the selective defluorination of a trifluoromethyl group from a commercially available trifluoromethyl group containing compounds in the presence of a metal center.[2]
Summary
The first metal free selective C–F bond activation of a CF3 group was observed with N-heterocyclic silylenes [PhC(NtBu)2SiCl] (1) and [CH{(CQCH2)(CMe)(2,6-iPr2C6H3N)2}Si] (2) with PhNQC(CF3)[2]. Metal free and selective activation of one C–F bond in a bound CF3 group†
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