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Synthesis of 1,2-Diphospholides Using a Main Group “Superbase”

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journal contribution
posted on 17.09.2018, 16:48 by Lily S. H. Dixon, Schirin Hanf, Jessica E. Waters, Andrew D. Bond, Dominic S. Wright
The synthesis of a range of 1,2-diphospholides can be achieved by a one-pot procedure involving the reactions of aromatic primary phosphines bearing ortho-CH2 substituents with the superbase mixture of nBuLi/Sb­(NMe2)3 in the presence of the Lewis base donor TMEDA (Me2NCH2CH2NMe2). The synthesis of the parent benzo-1,2-diphospholide and the substituted derivatives 4-methoxybenzo-1,2-diphospholide, 9-methylbenzo-1,2-diphospholide, and naphtho-1,2-diphospholide are reported from readily prepared primary phosphines. Bulk synthesis of the potassium salt of the previously reported 4,6-dimethylbenzo-1,2-diphospholide anion using this route provides a convenient starting material for reactivity studies.