Metal-Catalyzed Decarboxylative C–H Functionalization

Abstract

C-H bond activation and decarboxylation are two significant processes in organic synthesis. The combination of these processes provides a novel synthetic strategy, that is, decarboxylative C-H bond functionalization. Considerable attention has been focused on such an active research field. This review offers an overview of the utility of decarboxylative C-H bond functionalization in the synthesis of various organic compounds, such as styrenes, chalcones, biaryls, and heterocycles, covering most of the recent advances of the decarboxylative functionalization of Csp-H, Csp-H, and Csp-H bonds, as well as their scopes, limitations, practical applications, and synthetic potentials.

The use of carboxylic acids as traceless directing groups for regioselective C–H bond functionalisation

“…Within these specifications an attractive functionality is the carboxylate moiety. The abundancy of carboxylates in organic molecules and the versatility when considering further transformations 11 makes it an ideal candidate for directing C-H bond functionalisations; in addition the removal of the carboxylate by extrusion of CO 2 allows traceless operation of the directing group (Scheme 1(iv)).…”

MOF Decomposition and Introduction of Repairable Defects Using a Photodegradable Strut

“…Upon exposure to light, NPDAC decomposest o provide am ixture of photoproducts that includes 4-methyl-2nitrophenylacetic acid (3)w ith m/z 194.1,2 -nitro-p-xylene (4) with m/z 302.0 as ad imer ion, and 4-methyl-2-nitrobenzaldehyde (5)w ith m/z 164.0, which was determined by LC/MS analysis and verified by NMR spectroscopy.B ulk photolysis of NPDAC in D 2 Oa lso was monitored by 1 HNMR analysis.A fter 35 min of irradiation, the 1 HNMR spectrum shows am ixture of NPDAC and one major photoproduct, 4-methyl-2-nitrophenylacetic acid (3)t hat is produced by the photodecarboxylation characteristic of m-NPAA compounds. [41][42][43][44] Phenylacetic acids also can be converted directly to benzaldehyde derivatives with variousr eagents, [45][46][47] so the presence of 5 is unremarkable. During the irradiation, the clear yellowish solution becameo paque, which indicatest he possible formation of hydrophobic photoproducts.…”

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

“…Carboxylic acids are inexpensive, easily available compounds, and stable to air/moisture and thus are easy to handle. In the past decades, the employment of carboxylic acids as feedstock for organic synthesis has drawn considerable attention . Particularly, decarboxylative cascade cyclization reactions have emerged as a powerful method for organic synthesis .…”