Literature DB >> 26067204

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers.

Hang Shen1, Jiaqiang Li1, Qing Liu1, Jing Pan1, Ruofeng Huang1, Yan Xiong1,2.   

Abstract

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

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Year:  2015        PMID: 26067204     DOI: 10.1021/acs.joc.5b01102

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Sulfur(iv)-mediated umpolung α-heterofunctionalization of 2-oxazolines.

Authors:  Qifeng Zhang; Yuchen Liang; Ruiqi Li; Ziyi Huang; Lichun Kong; Peng Du; Bo Peng
Journal:  Chem Sci       Date:  2022-04-09       Impact factor: 9.969

Review 2.  Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling.

Authors:  Adriano Bauer; Nuno Maulide
Journal:  Chem Sci       Date:  2021-01-07       Impact factor: 9.825

  2 in total

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