Synthetic study demonstrates one-step synthesis of biphospholes in phosphole and aldimine systems, highlighting a cascade of sigmatropic shifts and dimerization.
Phospholes react with aldimines at 170 °C in the presence of mild Lewis acids to give C2-bridged biphospholes in good yields. The mechanism includes a series of [1,5] shifts of the P-substituents around the phosphole ring, a P-H + aldimine condensation, and the formation of a transient three-membered ring that dimerizes.
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Hu et al. (2015) studied this question.
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