I am trying to install a tetrazine group to an Aromatic electron-poor system with a phosphinate functional group. I am wondering if I can apply a lithiation reaction for this purpose?
Dear Mehrdad Shadmehr, please find attached an article entitled Lithiation of 3-aryl-1,2,4,5-tetrazines. The paper was published in Heterocyclic Communications 1998, 4, 301-308.The work shows that certain substituted 1,2,4,5-tetrazines can be lithiated while the tetrazine ring stays intact.
Thank you very much, Frank. I am wondering if I have a methyl, isopropyl, etc. on the 6 position. Can I apply Sec-Butyllithium for the lithiation reaction of the tetrazines followed by a nucleophilic attack to an electron-poor aromatic aldehyde?
Dear Mehrdad Shadmehr, I would just give it a try! After all, with methyl or isopropyl the 6-position of the tetrazine is also blocked. And why not try sec-butyllithium? If you find that it's too aggressive, commercially available LiN(SiMe3)2 might also be worth a try. Once the lithiation step works, the final reaction with an electron-poor aromatic aldehyde should be no problem Good luck!
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