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使用 - 杂环稳定的λ-碘烷将苄醇氧化为羰基化合物。

Oxidation of benzylic alcohols to carbonyls using -heterocyclic stabilized λ-iodanes.

作者信息

Kuczmera Thomas J, Puylaert Pim, Nachtsheim Boris J

机构信息

Institute for Organic and Analytical Chemistry, University of Bremen, Bremen, Germany.

Institute for Inorganic Chemistry and Crystallography, University of Bremen, Bremen, Germany.

出版信息

Beilstein J Org Chem. 2024 Jul 19;20:1677-1683. doi: 10.3762/bjoc.20.149. eCollection 2024.

DOI:10.3762/bjoc.20.149
PMID:39076300
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11285054/
Abstract

We present -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.

摘要

我们提出了 - 杂环稳定碘烷（NHIs）作为用于温和氧化活性醇的合适试剂。使用了两种不同的方案，均涉及通过氯化物添加剂进行活化，用于合成苄基酮和醛，且不会过度氧化，产率高达97%。基于质谱实验，提出了一种活性羟基（氯）碘烷作为反应中间体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/6cf01edf61d7/Beilstein_J_Org_Chem-20-1677-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/2add3a4a74bf/Beilstein_J_Org_Chem-20-1677-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/622cbd711604/Beilstein_J_Org_Chem-20-1677-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/5df5a7c79c4b/Beilstein_J_Org_Chem-20-1677-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/0b54afe8c81b/Beilstein_J_Org_Chem-20-1677-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/04746a4e948d/Beilstein_J_Org_Chem-20-1677-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/6cf01edf61d7/Beilstein_J_Org_Chem-20-1677-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/2add3a4a74bf/Beilstein_J_Org_Chem-20-1677-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/622cbd711604/Beilstein_J_Org_Chem-20-1677-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/5df5a7c79c4b/Beilstein_J_Org_Chem-20-1677-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/0b54afe8c81b/Beilstein_J_Org_Chem-20-1677-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/04746a4e948d/Beilstein_J_Org_Chem-20-1677-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/011c/11285054/6cf01edf61d7/Beilstein_J_Org_Chem-20-1677-g007.jpg

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