Synthesis of 1,2-Diphospholides Using a Main Group "superbase"
American Chemical Society (ACS)
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Dixon, L., Hanf, S., Waters, J., Bond, A., & Wright, D. (2018). Synthesis of 1,2-Diphospholides Using a Main Group "superbase". Organometallics, 37 (23), 4465-4472. https://doi.org/10.1021/acs.organomet.8b00480
The synthesis of a range of 1,2-diphospholides can be achieved by a one-pot procedure involving the reactions of aro-matic primary phosphines bearing ortho-CH2 substituents with the superbase mixture of nBuLi/Sb(NMe2)3 in the pres-ence 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 previ-ously reported 4,6-dimethylbenzo-1,2-diphospholide anion using this route provides a convenient starting material for reactivity studies.
The Cambridge Commonwealth European and International Trust Gonville and Caius College Cambridge The Studienstiftung des deutschen Volkes, Fonds of the Chemical Industry Selwyn College Cambridge (Walters-Kundert Studentship, J.E.W.).
External DOI: https://doi.org/10.1021/acs.organomet.8b00480
This record's URL: https://www.repository.cam.ac.uk/handle/1810/283126
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