The geometric structures of phosphorus-containing heterocycles

Arshinova, R. P.; Gubaidullin, R. N.; Ibragimova, S. D.; Mukmenev, E. T.

doi:10.1007/bf00947308

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2016

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“…The first challenge that needed to be addressed was the preparation of the spirocyclic secondary phosphite intermediate (Scheme ). Previously, this compound was generated by the treatment of PCl 3 with pentaerythritol, or through transesterification using diethylphosphite . In our hands, both of these approaches tended to generate intractable mixtures that were challenging to separate, and attempts at using these mixtures in the cross coupling reactions were low yielding.…”

Section: Resultsmentioning

confidence: 98%

Convenient Access to Arylated Spirocyclic Bisphosphonates

et al. 2016

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The synthesis of P-arylated spirocyclic bisphosphonates is described. The title compounds were generated through a process that combined transesterification with a palladium catalyzed P-arylation. The cross-coupling step could be carried out at room temperature using aryl iodides, while analogous reactions involving aryl bromides required heating. Nitrogen, oxygen, and sulfur containing heterocycles were also success-fully incorporated into the framework. Using this approach 20 new arylated compounds were generated bearing a range of electrophiles and functional groups. For the more reactive aryl iodides, the catalyst loading could be decreased to 0.3 % Pd per PÀH group in scaled-up versions of the method. The two-step process does not require the use of chlorophosphorus reagents.

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Section: Resultsmentioning

confidence: 98%