Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr3 and P(OMe)3 as the P(III) Source,The Journal of Organic Chemistry

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Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr3 and P(OMe)3 as the P(III) Source
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-10 , DOI: 10.1021/acs.joc.3c00567
Ang Li _{1,

2} , Fu-She Han _{1,

2}

Affiliation

An efficient method for the synthesis of 1-hydroxy-2,5-dihydrophosphole 1-oxides, a type of five-membered P-containing heterocyclic compound, is presented. The reaction was carried out through a [4C+1P] cyclization of 1,3-dienes with a combination of PBr₃ and P(OMe)₃ as the P^(III) source. To compare with the reported methods, the protocol reported herein not only is much milder and more rapid but also displays a broad substrate scope and affords the products in high yields (50–94%). In addition, the reaction could be reliably scaled up at the gram-scale level and was demonstrated to be a versatile platform for flexible derivatization. Consequently, this method provides a general and reliable way for the synthesis of five-membered phosphole derivatives.

中文翻译：

以PBr3和P(OMe)3为P(III)源，1,3-二烯[4C+1P]环化合成五元环次膦酸

提出了一种有效合成 1-羟基-2,5-二氢磷杂环化合物 1-氧化物（一种五元含磷杂环化合物）的方法。_{该反应以PBr 3}和P(OMe) ₃的组合作为P ^(III)源，通过1,3-二烯的[4C+1P]环化进行。与报道的方法相比，本文报道的方案不仅更温和、更快速，而且显示出广泛的底物范围并提供高产率的产品（50-94%）。此外，该反应可以可靠地放大到克级水平，并被证明是灵活衍生化的通用平台。因此，该方法为五元磷杂环戊烯衍生物的合成提供了一种通用且可靠的方法。

更新日期：2023-08-10

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