Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ3-iodanes

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-07-19 DOI:10.3762/bjoc.20.149
Thomas J. Kuczmera, Pim Puylaert, Boris J. Nachtsheim
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Abstract

We present N-heterocycle-stabilized iodanes (NHIs) as suitable reagents for the mild oxidation of activated alcohols. Two different protocols, both involving activation by chloride additives, were used to synthesize benzylic ketones and aldehydes without overoxidation in up to 97% yield. Based on MS experiments an activated hydroxy(chloro)iodane is proposed as the reactive intermediate.

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Beilstein J. Org. Chem. 2024, 20, 1677–1683. doi:10.3762/bjoc.20.149

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使用 N-杂环稳定λ3-碘烷将苄醇氧化为羰基化合物
摘要 我们提出了 N-杂环稳定碘烷(NHIs)作为活化醇温和氧化的合适试剂。我们采用两种不同的方案(均涉及氯化物添加剂的活化)合成了苄基酮和醛,且无过氧化反应,收率高达 97%。根据 MS 实验,活化的羟基(氯)碘烷被认为是反应中间体。Beilstein J. Org.2024, 20, 1677–1683. doi:10.3762/bjoc.20.149
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来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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