Tandem [5,5]-/[3,3]- rearrangements of aryl sulfoxides with allyl nitriles

Synthesis Pub Date : 2024-06-05 DOI:10.1055/a-2338-9005
Mengjie Hu, Liying Ru, Mengjiao Zhu, Shengwen Yang, Suojiang Fan, Jiangtao Ji, Dingming Zheng, Bo Peng
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Abstract

Tandem aromatic rearrangements can redirect the regioselectivity of original rearrangement and increase the complexity of products. Despite their obvious synthetic value, only few protocols of tandem aromatic rearrangements are reported. In this Article, we describe two new tandem aromatic rearrangements by using sulfonium rearrangements. Specifically, [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles followed by [3,3]-Cope rearrangement forges the tandem [5,5]-/[3,3]-rearrangements which affords ortho-functionalized phenyl sulfides as products. The other tandem rearrangement proceeds through [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles and the subsequent nuclephilic addition/DDQ-oxidation induced [3,3]-Cope rearrangement, which eventually achieves meta-functionalized phenyl sulfides as products.

Abstract Image

芳基硫醚与烯丙基腈的串联[5,5]-/[3,3]-重排反应
串联芳香重排可以改变原始重排的区域选择性,并增加产物的复杂性。尽管串联芳香重排具有明显的合成价值,但目前有关串联芳香重排的报道却很少。在本文中,我们介绍了利用锍重排进行的两种新的串联芳香重排。具体来说,苯硫醚与烯丙基腈发生[5,5]-重排,然后发生[3,3]-Cope 重排,形成串联[5,5]-/[3,3]-重排,生成正交官能化的苯硫化物作为产物。另一种串联重排是通过苯硫醚与烯丙基腈的[5,5]-重排,以及随后亲核加成/DDQ-氧化诱导的[3,3]-Cope 重排,最终得到元官能化的苯硫醚作为产物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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