Silver(i)-catalyzed stereoselective Meyer–Schuster-type rearrangement: synthesis of densely substituted α-iodo α,β-unsaturated thioesters
文献信息
发布日期
2023-12-07
DOI
10.1039/D3NJ05144G
影响因子
3.591
作者
José L. Lopes, Lucas L. Baldassari, Diogo S. Lüdtke
查看原文
摘要
Herein, we report our approach for a Meyer–Schuster type rearrangement to access α-iodo α,β-unsaturated thioesters from propargyl thioalkynes using a silver(I) catalyst and N-iodosuccinimide as an electrophilic iodine source. The reaction proceeds smoothly for a range of propargyl thioalkynes, thus delivering tri- and tetrasubstituted olefins in good yields and, for a number of examples, (Z)-selectivity. The silver catalyst presumably plays a dual role involving both the activation of the π-system by the alkynophilic Ag(I) and the activation of the NIS, ultimately leading to a sulfur-stabilized vinyl cation/ketenethionium intermediate. This reactive intermediate is trapped intramolecularly to yield an oxetane, which then readily undergoes decomposition to deliver the final product.
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来源期刊
New Journal of Chemistry
CiteScore:
5.3
自引率:
3.7%
年发文量:
2153
NJC (New Journal of Chemistry) is a broad-based primary journal encompassing all branches of chemistry and its sub-disciplines. It contains full research articles, communications, perspectives and focus articles. This well-established journal, owned by the Centre National de la Recherche Scientifique (CNRS) of France, has been co-published with the Royal Society of Chemistry since January 1998. NJC is the forum for the publication of high-quality, original and significant work that opens new directions in chemistry or other scientific disciplines. In addition to having a significant chemical component, work published in NJC must demonstrate that it will have an impact on areas of research other than that of the reported work.
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