Hypervalent Iodine Catalyzed Hofmann Rearrangement of Carboxamides Using Oxone as Terminal Oxidant
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- 作者：Akira Yoshimura ; Kyle R. Middleton ; Matthew W. Luedtke ; Chenjie Zhu ; Viktor V. Zhdankin
- 刊名：The Journal of Organic Chemistry
- 出版年：2012
- 出版时间：December 21, 2012
- 年：2012
- 卷：77
- 期：24
- 页码：11399-11404
- 全文大小：277K
- 年卷期：v.77,no.24(December 21, 2012)
- ISSN：1520-6904
文摘
Hofmann rearrangement of carboxamides to carbamates using Oxone as an oxidant can be efficiently catalyzed by iodobenzene. This reaction involves hypervalent iodine species generated in situ from catalytic amount of PhI and Oxone in the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) in aqueous methanol solutions. Under these conditions, Hofmann rearrangement of various carboxamides affords corresponding carbamates in high yields.