Abstract
3d transition metals-catalyzed C–H bond functionalizations represent nowadays an important tool in organic synthesis, appearing as the most promising alternative to cross-coupling reactions. Among 3d transition metals, iron found widespread application due to its availability and benign nature, and it was established as an efficient catalyst in organic synthesis. In this context, the use of ortho-orientating directing groups (DGs) turned out to be necessary for promoting selective iron-catalyzed C–H functionalization reactions. Very recently, triazoles DGs were demonstrated to be more than an excellent alternative to the commonly employed 8-aminoquinoline (AQ) DG, as a result of their modular synthesis as well as the mild reaction conditions applied for their removal. In addition, their tunable geometry and electronics allowed for new unprecedented reactivities in iron-catalyzed C–H activation methodologies that will be summarized within this review.
Highlights
Transition metals-catalyzed cross-coupling reactions are a powerful tool in organic synthesis.Since pioneering works in the 1940s [1], and afterwards on modern palladium catalysis [2], they continue to play an important role for the construction of new C–C bonds [3,4]
We aim to offer to themotif, reader a complete overviewof of new the synthetic interplay of electronic and steric properties of the triazole with the introduction families possibility of 1,2,3-triazole directing-groups in the of iron-catalyzed functionalizations
The TAM directing groups (DGs) allowed the synthesis of a family of ortho-alkynylated carboxamides 31 and site selectivity (Scheme 17)
Summary
Transition metals-catalyzed cross-coupling reactions are a powerful tool in organic synthesis. This class of DGs could be installed and subsequently cleaved under mild reaction conditionsthis with a wide functional group to the synthesis of key organic. Group tolerance,From leading to the synthesis of keythe organic generation of TAMBn to wasfurther demonstrated to be a widely applicable for iron-catalyzed molecules amenable structural modifications. DGs. Within this review, we aim to offer to themotif, reader a complete overviewof of new the synthetic interplay of electronic and steric properties of the triazole with the introduction families possibility of 1,2,3-triazole directing-groups in the of iron-catalyzed functionalizations. Of triazole-based this review, we aimfield to offer to the reader C-H a complete overview of the synthetic possibility of 1,2,3-triazole directing-groups in the field of iron-catalyzed C‒H functionalizations
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