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

引用次数: 0

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

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

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