Tandem [5,5]-/[3,3]-Rearrangements of Aryl Sulfoxides with Allyl Nitriles

被引：0

作者：

Hu, Mengjie ^{[1
]}

Ru, Liying ^{[1
]}

Zhu, Mengjiao ^{[1
]}

Yang, Shengwen ^{[1
]}

Fan, Suojiang ^{[1
]}

Ji, Jiangtao ^{[1
]}

Zheng, Dingming ^{[1
]}

Peng, Bo ^{[1
]}

机构：

[1] Zhejiang Normal Univ, Key Lab Minist Educ Adv Catalysis Mat, Jinhua 321004, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 19期

基金：

中国国家自然科学基金;

关键词：

aromatic Claisen rearrangement; 5,5]-rearrangement; tandem rearrangement; sulfur; nitrile; ACCELERATED CLAISEN REARRANGEMENT; NUCLEOPHILIC ORTHO-ALLYLATION; ALPHA-ARYLATION; CATALYSIS; CASCADES; DESIGN; COPE;

D O I：

10.1055/a-2338-9005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem aromatic rearrangements represent a potent strategy for modulating the regioselectivity of a rearrangement process. In this article, we disclose two novel tandem aromatic rearrangements triggered by sulfonium [5,5]-rearrangement recently developed in our laboratory. Specifically, the [5,5]-rearrangement of aryl sulfoxides with allyl nitriles, followed by [3,3]-Cope rearrangement, forges a seamless tandem [5,5]-/[3,3]-rearrangement cascade, affording ortho-functionalized aryl sulfides. The other tandem process involves [5,5]-rearrangement of aryl sulfoxides with allyl nitriles, followed by nucleophilic addition/DDQ-oxidation-induced [3,3]-Cope rearrangement, eventually yielding meta-functionalized aryl sulfides. Both consecutive rearrangements enrich the repertoire of tandem aromatic rearrangement methodologies.

引用

页码：2973 / 2984

页数：12

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