A general approach to substituted diphenyldiazenes

作者：Lutz Toni A; Spanner Patrick; Wanner Klaus T

来源：Tetrahedron, 2016, 72(12): 1579-1589.

DOI：10.1016/j.tet.2016.02.011

• Substituted diphenyldiazenes
• Azo coupling
• N,N-Diallyl protection group
• Cleavage of N,N-diallyl groups (deallylation)
• Photoswitchable ligands

A general and practical synthetic method for the construction of unsymmetrically substituted diphenyldiazenes based on classical azo coupling reaction has been developed. A key feature of this method is the use of N,N-diallyl protected aniline derivatives as coupling components. The N,N-diallyl moiety of the coupling component warrants sufficient reactivity and allows to avoid formation of constitutional isomers resulting from intermediate triazene formation. Furthermore, subsequent to the coupling reaction, the N,N-diallyl aminofunction, can be replaced by other substituents including hydrogen via diazonium ion intermediates. In general, following this approach target compounds can be obtained in reasonable to good yields.

• 出版日期2016-3-24