Shahsavari Shahien, Gooding James, Wigstrom Travis, Fang Shiyue
Department of Chemistry Michigan Technological University 1400 Townsend Drive, Houghton, MI 49931.
ChemistrySelect. 2017 May 2;2(13):3959-3963. doi: 10.1002/slct.201700364. Epub 2017 May 10.
Hindered --alkyl -arylcarbamates were conveniently prepared by treating arylamines with aryl -alkyl carbonates in the presence of a strong base. The new method avoids the use of sensitive and difficult-to-access dialkyl dicarbonates and isocyanates, which are most commonly used in known methods. Instead, the stable and readily accessible alkyl aryl carbonates are used. Therefore, the new method is particularly suitable for the synthesis of -arylcarbamates that contain a complex -alkyl moiety. Using the method, electron-rich and electron-poor, and primary and secondary arylamines can all be conveniently converted to their carbamates with acceptable yields. The method was also found equally effective for the synthesis of the less hindered -secondary and -primary alkyl -arylcarbamates.
受阻的烷基芳基氨基甲酸酯可通过在强碱存在下用芳基烷基碳酸酯处理芳胺方便地制备。该新方法避免了使用已知方法中最常用的敏感且难以获得的二烷基二碳酸酯和异氰酸酯。相反，使用了稳定且易于获得的烷基芳基碳酸酯。因此，该新方法特别适用于合成含有复杂烷基部分的芳基氨基甲酸酯。使用该方法，富电子和缺电子的以及伯芳胺和仲芳胺都可以方便地以可接受的产率转化为它们的氨基甲酸酯。还发现该方法对于合成位阻较小的仲烷基和伯烷基芳基氨基甲酸酯同样有效。
