Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

被引:269
作者
Brand, Jonathan P. [1 ]
Gonzalez, Davinia Fernandez [1 ]
Nicolai, Stefano [1 ]
Waser, Jerome [1 ]
机构
[1] EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, BCH 4306, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
HYDROXYLATIVE PHENOL DEAROMATIZATION; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; GACL3-CATALYZED ORTHO-ETHYNYLATION; CATALYZED DIRECT ALKYNYLATION; IODOXYBENZOIC ACID IBX; ORGANIC-SYNTHESIS; POLYVALENT IODINE; SYNTHETIC UTILITY; OXIDATIVE DEAROMATIZATION; TERT-BUTYLPEROXYIODANES;
D O I
10.1039/c0cc02265a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
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页码:102 / 115
页数:14
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