The Regitz diazo transfer and C-C bond cleavage were the key steps of this transformation, which provided diverse carbonyl-substituted structural 1,2,3-triazoles. This reaction featured with excellent regioselectivity, wide functional group tolerance, and mild conditions....
Regitz重氮转移法 Regitz Diazo Transfer 概要 活性亚甲基化合物可以通过与磺酰叠氮化物反应转化为重氮化合物。 这些重氮化合物可以作为、1,3-Dipolar、或者金属卡宾的前体使用。后者可以进行Cyclopropanation与C-H卡宾插入反应。 基本文献 Dimroth, O. et al.Ann.1910,373, 336. Regitz, M.Ann.1964,676, 101. ...
and β-iminoketones. Secondary reactions can lead to azo compounds and heterocycles such as 1,2,3-triazoles, 1,2,3-thiadiazoles, and pyrazolin-4-ones. Azidinium salts react in the same way, but in this case an acidic reaction medium is necessary, a fact that is sometimes advantageous....
Reaction Mechanism Examples The diazo transfer does not occur at the α-position of simple ketones, and in those cases, the pre-introduction of formyl group is an effective approach.[1]Trifluroacetyl group can be used for the same purpose for more sensitive compounds.[2] ...
For the sake of completeness, we had attempted the sulfonyl-azide-free (SAFE) aqueous-phase diazo transfer reaction, but we found a lower yield (70%) with that process. Over-all, the optimized conditions include use of 1.5 equivalents of Hunig's base and 1.5 equivalents of p-toluenesulfonyl...