Iron(iii) chloride in oxidative C–C coupling reactions

Abstract

In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access to structurally well-defined oligo- and polymers. Iron(III) chloride is commercially available and inexpensive. Being a mild oxidising agent it has been applied in numerous reactions leading to new carbon-carbon-bonds in complex molecular arrays (107 references).

Reactions of [FeL2(CH3CN)2](PF6)2 (L = N-pyrimid-2-ylimidazol-ylidene) with N-, P-, O-, and S-donors and its catalytic activity

“…A solution of Grignard reagent (2.0 mL, 1.0 mol/L in THF) at room temperature was added to the solution of 1 in one portion with stirring. After 12 h, a saturated aqueous solution of NH 4 Cl was added to quench the reaction. The mixture was extracted with CH 2 Cl 2 (3 × 10 mL), and the combined organic layer was dried over MgSO 4 .…”

“…After 12 h, a saturated aqueous solution of NH 4 Cl was added to quench the reaction. The mixture was extracted with CH 2 Cl 2 (3 × 10 mL), and the combined organic layer was dried over MgSO 4 . After removal of solvent, the crude product was purified by column chromatography on silica gel to afford the desired product.…”

“…Interest in the catalytic applications of iron in organic synthesis has increased in recent years [1][2][3][4][5][6]. In earlier studies, we found that functionalized N-heterocyclic carbenes (NHCs) were good ligands in homogeneous catalysis because of strong donating abilities [7][8][9][10][11].…”

Efficient Lewis acid-assisted Brønsted acid (LBA) catalysis in the iron-catalyzed Friedel-Crafts alkylation reaction of indoles

“…However, some drawbacks still exits in previous synthetic methods, e.g., the necessity to utilize expensive stoichiometric amounts of Lewis acidic catalysts and toxic heavy metals, which does not meet the contemporary requirement for green chemistry. Among transition metal salts, iron(III) chloride is a very cheap and efficient Lewis acid catalyst, and has attracted much attention in a great deal of useful organic transformations [16][17][18]. With our continuous research in iron catalysis, herein, we wish to report some findings in the iron-catalyzed Friedel-Crafts alkylation of indoles.…”

Recent advances in the iron-catalyzed C-C bond formation via polar reactions of alcohols with carbon-centered nucleophiles

“…However, very few successful systems to generate a C-C bond by using alcohols as alternatives to halides as coupling partners have been achieved due to the poor leaving ability of the hydroxyl group [3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Recently, some efficient iron-catalyzed methods to form C-C bonds via polar reactions of alcohols with various carbon-centered nucleophiles have been developed.…”