Recent advances in transition metal-catalyzed C–H bond functionalization of ferrocene derivatives

Abstract

5Transition metal-catalyzed C-H bond functionalizations of ferrocene derivatives have emerged in the last few years as a versatile tool in synthetic organometallic chemistry. These protocols offer significant advantages over more traditional approaches for the synthesis of functionalized ferrocene derivatives in terms of both atom-and step-economy. In this Perspective, we aim to showcase the state of the art in this field, with special emphasis on recent asymmetric methodologies.

Regioselective addition/annulation of ferrocenyl thioamides with 1,3-diynes via a sulfur-transfer rearrangement to construct extended π-conjugated ferrocenes with luminescent properties

“…Recently, chelating-assisted C-H bond functionalization has made signicant advances, [18][19][20][21][22][23][24][25] which provide new opportunities for the rapid construction of 1,2-disubstituted ferrocenes. [26][27][28][29][30][31][32][33][34][35][36] 1,3-Diynes are an important class of organic architectures and have been widely used in the construction of various ve-membered heteroaromatic rings via the reaction with heteroatoms. [37][38][39][40] However, it is still a challenging task to control the regioselectivity in the migratory insertion of 1,3diyne into the carbon-metal bond.…”

Enantioselective deprotometalation of N,N-dialkyl ferrocenecarboxamides using metal amides

“…Ferrocene-containing compounds have been used in different fields such as catalysis, material sciences and medicinal chemistry; thus, many efforts have been devoted to the development of efficient syntheses to produce these important substrates. 1 Among the existing ways to achieve ferrocene C-H bond functionalization, transition metal-catalyzed reactions have recently emerged, [2][3] with possible extensions to enantioselective versions. 4 However, the most efficient methods imply the use of expensive catalytic sources (e.g.…”

Methylation of Arenols through Ni‐catalyzed C—O Activation with Methyl Magnesium Bromide

“…[6d] To our delight, this protocol was suitable to ferrocene motif (12b), which was frequently used in a range of fields, including material science, [15] medicinal chemistry, [16] organic catalyst and ligand scaffold. [17] Another feature of this method was its good compatibility in the nitrogen-containing heterocycles, such as pyrrolyl (13b), tetrahydroquinolinyl (14b), piperazinyl (15b), and piperidinyl (16b). On the other hand, a good yield was obtained with the extented π-conjugated system (17b).…”