Defined Hypervalent Iodine(III) Reagents Incorporating Transferable Nitrogen Groups: Nucleophilic Amination through Electrophilic Activation

被引:115
作者
Souto, Jose A. [1 ]
Martinez, Claudio [1 ]
Velilla, Irene [1 ]
Muniz, Kilian [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
关键词
amides; amination; iodine(III) reagents; nucleophilicity; oxidation; METAL-FREE CONDITIONS; N BOND FORMATION; CYCLOFUNCTIONALIZATION TOTAL-SYNTHESIS; TRIISOPROPYLSILYL ENOL ETHERS; ACID-CATALYZED REARRANGEMENT; BETA-AZIDO FUNCTIONALIZATION; MEDIATED ALKYNE AMIDATION; POLYVALENT IODINE; C-H; TRIMETHYLSILYL AZIDE;
D O I
10.1002/anie.201206420
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Only I and N: Hypervalent iodine(III) reagents with two reactive I-N single bonds have been isolated for the first time. Their solid-state and solution structures provide evidence for enhanced electrophilicity at iodine and nucleophilic character of the imine. As a result, improved reactivity in amination reactions and unprecedented nitrogen-transfer reactions under metal-free conditions are realized. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
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页码:1324 / 1328
页数:5
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