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Article Dans Une Revue Dalton Transactions Année : 2024

Molecular Engineering of 3-Arylated Tetrazo[1,2-b]indazoles: Divergent Synthesis and Structure-property Relationships

Marie Cordier

Résumé

The synthetic scope of 3-arylated tetrazo[1,2-b]indazoles is reported based on a Pd-catalyzed Liebeskind–Srogl cross-coupling reaction followed by an N-cyclisation process. The reactivity of the nitrogen atoms was used to further diversify these N-rich polyaromatic tetrazo[1,2-b]indazoles in a panel of reactions (protonation, selective oxidation, metallations). Selective ortho-C–H activation/functionalization on the heterocycle was also demonstrated with three transition metals (TM = Pd, Ir and Rh). The effects of all these molecular engineering strategies, particularly the N-modifications, on the optical and redox properties of the 3-arylated tetrazoindazoles were studied experimentally and theoretically. This study highlights the diversity of molecular structures and electronic properties offered by the tetrazo[1,2-b]indazole platform.

Domaines

Chimie organique
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Dates et versions

hal-04599869 , version 1 (25-06-2024)

Identifiants

Citer

Asmae Bousfiha, Oumaima Abidi, Louis Lemetayer, Navya Sood, Iogann Tolbatov, et al.. Molecular Engineering of 3-Arylated Tetrazo[1,2-b]indazoles: Divergent Synthesis and Structure-property Relationships. Dalton Transactions, 2024, 53 (25), pp.10737. ⟨10.1039/D4DT01122H⟩. ⟨hal-04599869⟩
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