Abstract
C–H activation with transition metal catalysis has become an important tool in organic synthesis for the functionalization of low reactive bonds and the preparation of complex molecules. The choice of the directing group (DG) proves to be crucial for the selectivity in this type of reaction, and several different functional groups have been used efficiently. This review describes recent advances in C–H functionalization of aromatic rings directed by a N-tosylcarboxamide group. Results regarding alkenylation, alkoxylation, halogenation, and arylation of C–H in the ortho position to the tosylcarboxamide are presented. Moreover, the advantage of this particular directing group is that it can undergo further transformation and act as CO or CON fragment reservoir to produce, in sequential fashion or one-pot sequence, various interesting (hetero)cycles such as phenanthridinones, dihydroisoquinolinones, fluorenones, or isoindolinones.
Highlights
Over the last few years, the direct functionalization of C–H bonds has become an essential chemical transformation in organic synthesis
A second part of the review is devoted to the construction of five- and six-membered rings using the N-tosylcarboxamide (CONHTs) TDG jointly as directing group and as CO or CON
A second part of the review is devoted to the construction of five- and sixmembered rings using the N-tosylcarboxamide (CONHTs) TDG jointly as directing group and as CO
Summary
Over the last few years, the direct functionalization of C–H bonds has become an essential chemical transformation in organic synthesis. Recent advances in the C–H activation/transformations allow these methodologies to be integrated into multi-step sequences, to be used on poly-substituted substrates, in late-stage functionalization strategies, and even in total synthesis [1,2,3] In this context, the functionalization of aromatic rings by the selective activation of carbon–hydrogen bonds has experienced unprecedented growth for two decades. A second part of the review is devoted to the construction of five- and six-membered rings using the N-tosylcarboxamide (CONHTs) TDG jointly as directing group and as CO or CON fragment reservoir (Scheme 2 (e–h)). Scope ofUsing the reaction promoted by N-tosylcarboxamide (CONHTs) as directing group
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