Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions.
In the last decades, hypervalent iodine reagents have raised from chemical curiosities to mainstream reagents in organic synthesis. The use of benziodoxole-derived reagents has been especially successful in oxidation methods, whereas non-cyclic iodinanes have been used both for oxidation and atom-transfer reactions. On the other hand, the exceptional properties of benziodoxole reagents for atom-transfer reactions have only started to attract the attention of the synthetic community more recently. In this review, progress in the use of these compounds for C-X and C-C bond formations will be presented. In particular, recent breakthroughs in trifluoromethylation and alkynylation reactions have been realized since 2006 based on benziodoxole-derived reagents and these results are the main focus of this article.
Brand
Jonathan P
JP
Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (CH), Switzerland.
Fernández González
Davinia
D
Nicolai
Stefano
S
Waser
Jérôme
J
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D008745:Methylation; D010084:Oxidation-Reduction
D000480:Alkynes; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D007462:Iodobenzenes; D007463:Iodobenzoates; C476101:o-iodoxybenzoic acid