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Amino and Alkyl B-Substituted P-Stabilized Borenium Salts.

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Title: Amino and Alkyl B-Substituted P-Stabilized Borenium Salts.
Authors: Devillard, Marc1, Bouhadir, Ghenwa1, Mallet-Ladeira, Sonia2, Miqueu, Karinne3, Bourissou, Didier1 dbouriss@chimie.ups-tlse.fr
Source: Organometallics. Nov2016, Vol. 35 Issue 21, p3788-3794. 7p.
Subjects: Amino compounds, Alkyl compounds, Borenium ions, Functional groups, Benzene, Solution (Chemistry)
Abstract: The ability of the phosphino-naphthyl moiety to stabilize amino- and alkylborenium cations has been studied. Surprisingly, the phosphine-aminochloroborane precursor 2 was found to exist in neutral open form (without P-B interaction) in benzene solution and in the solid state but to ionize spontaneously in chloroform to generate the P-stabilized borenium salt 3. Addition of gallium trichloride shifts the process forward and affords the corresponding tetrachlorogallate borenium salt 3'. The phosphine group of 2 remains available for external reactivity, as shown by the ready formation of the corresponding phosphine gold(I) chloride complex 4. The P-stabilized cyclohexylborenium cation 6 has also been prepared by reacting the corresponding bromoborane 5 with gallium tribromide. Compound 6 is a very rare example of an alkyl-substituted borenium salt. The structures of 2, 3', and 4-6 have been unambiguously ascertained by multinuclear NMR spectroscopy and X-ray crystallography. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:The ability of the phosphino-naphthyl moiety to stabilize amino- and alkylborenium cations has been studied. Surprisingly, the phosphine-aminochloroborane precursor 2 was found to exist in neutral open form (without P-B interaction) in benzene solution and in the solid state but to ionize spontaneously in chloroform to generate the P-stabilized borenium salt 3. Addition of gallium trichloride shifts the process forward and affords the corresponding tetrachlorogallate borenium salt 3'. The phosphine group of 2 remains available for external reactivity, as shown by the ready formation of the corresponding phosphine gold(I) chloride complex 4. The P-stabilized cyclohexylborenium cation 6 has also been prepared by reacting the corresponding bromoborane 5 with gallium tribromide. Compound 6 is a very rare example of an alkyl-substituted borenium salt. The structures of 2, 3', and 4-6 have been unambiguously ascertained by multinuclear NMR spectroscopy and X-ray crystallography. [ABSTRACT FROM AUTHOR]
ISSN:02767333
DOI:10.1021/acs.organomet.6b00737