Efficient Pd-Catalyzed Coupling Reaction of Cationic Cyclopentadienyliron Complexes of Chloro-substituted Arenes with Arylboronic Acid

Abstract

Cationic cyclopentadienyliron complexes of chloro-substituted arenes were found to perform efficient Pd-catalyzed cross-coupling reactions with arylboronic acids under mild conditions. Using this method, some new cationic cyclopentadienyliron complexes of biaryl derivatives (Fc−Bi) were obtained with good yields. After a photolysis reaction of the obtained Fc−Bi, some biaryl derivatives were easily obtained. Results in the present study provided a practical route to the preparation of Fc−Bi and biaryl derivatives.

Generation of Cyclopentadiene for Diels–Alder Reactions by Visible‐Light Irradiation of Iron Sandwich Complexes

“…[12][13][14][15] This ability has been used in organic synthesis for modification and further libera-tion of the arene ligands. In particular, polycyclic arenes, [16,17] cyclophanes, [18] dendrimers, [19] and polymers [20] have been synthesized this way. On the other hand, the same photochemical reaction has been used in organometallic chemistry for the synthesis of (C 5 R 5 )Fe(L) x complexes with various Supporting information for this article is available on the WWW under https://doi.org/10.1002/hlca.202100246 ligands.…”

Hydrophilic Pd/MgO Nanosystem for the Highly Efficient Aqueous-Phase Catalysis of Suzuki–Miyaura Reactions

“…Palladium-catalyzed Suzuki coupling reaction has become one of the most effective and important methods for making C–C bonds since the first report in 1979. − The coupling reaction of aryl halides with organoboron reagents that features extensive substrate applicability and functional group tolerance has been widely applied in the synthesis of versatile natural products, pharmaceuticals, and functional materials. − Currently, homogeneous palladium-based catalysts, such as palladium salts with phosphine ligands or N -heterocyclic carbene ligands, have still been the most widely used catalysts, and products with desirable yields and efficiencies have been achieved. − Nevertheless, they suffer from intrinsic deficiency in product separation and catalyst recycling, which significantly restricted their large-scale industrial application. Besides, most Suzuki coupling reactions have been currently performed in large amounts of organic solvents ( N , N -dimethylformamide (DMF), tetrahydrofuran (THF), 1,4-dixoane, and so forth), which are toxic and harmful to the environment. − Therefore, out of academic and industrial research, a heterogeneous supported palladium catalyst that exhibits high catalytic activities and is easy to recycle when operated in green solvents, particularly in water, to realize green and efficient synthesis is urgently needed.…”

Synthesis and Characterization of Novel 1,4-Bis(carbazolyl)benzene Derivatives with Blue-Violet Two-Photon-Excited Fluorescence

“…This process involves a nucleophilic substitution between the cyclopentadienyliron complexes of chloroarenes and carbazole or hydroxylcarbazole, followed by photolysis of cyclopentadienyliron complexes of arylated carbazoles. The process combines two steps in good yields and is cost-effective. , …”

“…The process combines two steps in good yields and is cost-effective. 22,23 In the design of the π-conjugated compounds, phenylacetylene is an important unsaturated backbone linkage. The linkage is rigid, has large π-electron delocalization, and is sterically less demanding.…”