Literature DB >> 26920160

Hypervalent Iodine-Induced Oxidative Couplings (New Metal-Free Coupling Advances and Their Applications in Natural Product Syntheses).

Toshifumi Dohi1, Yasuyuki Kita2,3.   

Abstract

Recently, hypervalent iodine reagents have been extensively used in organic synthesis. A variety of reactions available for natural product syntheses have been developed using phenyliodine(III) diacetate (PIDA), phenyliodine(III) bis(trifluoroacetate) (PIFA), and other iodine(III) and (V) reagents. These reactions are expected to have applications in pharmaceutical and agrochemical processes because of their safety, mild reaction conditions, and high yields of pure products. Under such considerations, this chapter focuses on the oxidative coupling reactions of hypervalent iodine reagents found in total syntheses of biologically active natural products and their related compounds.

Entities:  

Keywords:  Hypervalent iodine reagents; Natural products; Oxidative coupling; Total synthesis

Mesh:

Substances:

Year:  2016        PMID: 26920160     DOI: 10.1007/128_2016_667

Source DB:  PubMed          Journal:  Top Curr Chem        ISSN: 0340-1022


  5 in total

Review 1.  "Cut and Paste" Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles.

Authors:  Marina Porras; Dácil Hernández; Concepción C González; Alicia Boto
Journal:  Front Chem       Date:  2022-05-18       Impact factor: 5.545

2.  Selective carboxylation of reactive benzylic C-H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system.

Authors:  Toshifumi Dohi; Shohei Ueda; Kosuke Iwasaki; Yusuke Tsunoda; Koji Morimoto; Yasuyuki Kita
Journal:  Beilstein J Org Chem       Date:  2018-05-16       Impact factor: 2.883

3.  Iminoxyl radicals vs. tert-butylperoxyl radical in competitive oxidative C-O coupling with β-dicarbonyl compounds. Oxime ether formation prevails over Kharasch peroxidation.

Authors:  I B Krylov; S A Paveliev; N S Shumakova; M A Syroeshkin; B N Shelimov; G I Nikishin; A O Terent'ev
Journal:  RSC Adv       Date:  2018-02-05       Impact factor: 3.361

Review 4.  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

5.  The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX.

Authors:  Md Toufique Alam; Saikat Maiti; Prasenjit Mal
Journal:  Beilstein J Org Chem       Date:  2018-09-12       Impact factor: 2.883

  5 in total

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