The Gomberg-Bachmann reaction for the arylation of anilines with aryl diazotates.

The Gomberg-Bachmann reaction for the arylation of anilines with aryl diazotates.
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DOI:
10.1002/chem.201200430
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发表时间:
2012-09
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通讯作者:
Gerald Pratsch;Tina Wallaschkowski;M. Heinrich
Gerald Pratsch;Tina Wallaschkowski;M. Heinrich
中科院分区:
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文献类型:
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作者:
Gerald Pratsch;Tina Wallaschkowski;M. Heinrich

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简单的氢氧化钠水溶液足以排除离子副反应,并通过Gomberg-Bachmann反应的新变种从芳基重氮酸盐和苯胺制备2-氨基联苯(见方案)。在碱性条件下的无金属反应首次利用了苯胺的游离氨基的高度稳定作用,这导致了到目前为止还没有达到的区域选择性。
Simply aqueous sodium hydroxide is sufficient to exclude ionic side reactions and to prepare 2-aminobiphenyls from aryl diazotates and anilines through a new variant of the Gomberg-Bachmann reaction (see scheme). The metal-free reaction under basic conditions allows to exploit the highly radical-stabilizing effect of the aniline's free amino function for the first time, which leads to a so far unreached regioselectivity.