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NHC催化的邻二酮和三酮的裂解,随后烯酮和炔酮插入。

NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones.

作者信息

Takaki Ken, Hino Makoto, Ohno Akira, Komeyama Kimihiro, Yoshida Hiroto, Fukuoka Hiroshi

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8527, Japan.

出版信息

Beilstein J Org Chem. 2017 Aug 30;13:1816-1822. doi: 10.3762/bjoc.13.176. eCollection 2017.

DOI:10.3762/bjoc.13.176
PMID:28904625
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5588593/
Abstract

Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave α,β-double acylation products via unique Breslow intermediates isolable as acid salts, whereas the triketones formed stable adducts with the NHC instead of the coupling products.

摘要

已对噻唑鎓卡宾催化的1,2 - 二酮和1,2,3 - 三酮与烯酮和炔酮的反应进行了研究。二酮通过可作为酸盐分离的独特布雷斯洛中间体生成α,β - 双酰化产物,而三酮与氮杂环卡宾形成稳定的加合物而非偶联产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/d0b48d30e3bf/Beilstein_J_Org_Chem-13-1816-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/9b0a9d0c2e1f/Beilstein_J_Org_Chem-13-1816-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/f711aa18a020/Beilstein_J_Org_Chem-13-1816-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/45b27c8cb4bb/Beilstein_J_Org_Chem-13-1816-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/993043ef75cd/Beilstein_J_Org_Chem-13-1816-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/781642f44002/Beilstein_J_Org_Chem-13-1816-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/d0b48d30e3bf/Beilstein_J_Org_Chem-13-1816-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/9b0a9d0c2e1f/Beilstein_J_Org_Chem-13-1816-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/f711aa18a020/Beilstein_J_Org_Chem-13-1816-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/45b27c8cb4bb/Beilstein_J_Org_Chem-13-1816-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/993043ef75cd/Beilstein_J_Org_Chem-13-1816-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/781642f44002/Beilstein_J_Org_Chem-13-1816-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7144/5588593/d0b48d30e3bf/Beilstein_J_Org_Chem-13-1816-g003.jpg

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