N-Tosylcarboxamide in C–H Functionalization: More than a Simple Directing Group

Processes

Benjamin Large¹  Damien Prim¹  Vincent Terrasson² 

[1] Institut Lavoisier de Versailles, UVSQ, CNRS, Université Paris-Saclay, 78035 Versailles, France;TIMR (Integrated Transformations of Renewable Matter), ESCOM, Centre de Recherche de Royallieu, Université de Technologie de Compiègne, CS 60319, 60203 Compiègne CEDEX, France;

关键词: C–H functionalization;    catalysis;    directing group;    tosylbenzamide;   

DOI  :  10.3390/pr8080981

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown