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We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl3 and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2-naphthols or 2-naphthylamines using simple and cheap catalysts. Several control experiments supported the hypothesis that a redox reaction between Fe(III) and KI produces I2, which catalyzed the chalcogenylation.

The oxidative radical cyclization of active methylene derivatives containing allyl groups as radical acceptors proceeded with the use of FeCl3 as a mild oxidant. The FeCl3-promoted cyclization reactions of α-substituted active methylene compounds provide a synthetic approach to various γ-lactams containing a quaternary carbon atom.

A straightforward and concise method was developed for the efficient and rapid synthesis of iodo-3H-pyrazoles by the FeCl3/I2-mediated propargylic substitution of tertiary propargylic alcohols with p-toluenesulfonyl hydrazide and subsequent cyclization under mild conditions. The method constitutes a novel approach to the synthesis of various iodo-3H-pyrazoles with a wide substrate scope and in high yields.

A general, facile, and efficient method is presented for the synthesis of 3-substituted 1,2,4-oxadiazoles from amidoximes and triethyl orthoformate. The procedure employs an iron(III) chloride/ l -proline catalytic system and the 3-substituted 1,2,4-oxadiazole products are obtained in moderate to good yields.

Catalytic synthesis of N-benzothiazol-2-yl-amides from 1-acyl-3-(phenyl)thioureas was achieved in the presence of an iron catalyst through C(sp2)–H functionalization and C–S bond formation. Various N-benzothiazol-2-yl-amides were selectively obtained in good yields.

The FeCl3-mediated condensation of an α-phenylenamino ester and an enone proceeds efficiently to afford a 2-phenylnicotinate. The subsequent intramolecular Friedel–Crafts reaction yielded an ­onychine framework. Modifications at the 2-, 3-, and 8-positions of the onychine framework were easily achieved by altering the enamino esters­ and enones, which facilitated the discovery of potentially bioactive compounds.

Potentially bioactive angular dihydropyridocoumarin and phenanthrolinone derivatives are synthesized in good to excellent yields using readily available iron(III) chloride (FeCl3) as the catalyst. The process is very simple, straightforward and inexpensive, and provides a diverse range of pyranoquinolone or phenan­throlinone derivatives, via a 6-endo-dig mode of cyclization, starting from simple and easily available 6-(N-propargyl)aminocoumarin and -quinolone derivatives.

A simple and highly efficient synthesis of 2-substituted quinazolin-4(3H)-ones by the iron(III) chloride catalyzed reaction of isatoic anhydride with various amidoxime derivatives was developed. Several aryl and alkyl amidoximes were screened to demonstrate the scope of the methodology.

Iron(III) chloride-catalyzed direct amination of electron-rich arenes with azodicarboxylates gives the corresponding aryl hydrazides in moderate to good yields within two minutes under mild conditions. This method will serve as an important tool for the synthesis of bioactive nitrogen-containing products and pharmaceuticals.

Polycyclic aromatics have attracted much research interest owing to their promising applications in supramolecular chemistry and organic electronics. Much research focuses on developing novel polycyclic aromatics with diverse properties. Among various synthetic methodologies for constructing polycyclic aromatics, iron(III) chloride (FeCl3) promoted cyclization has been extensively utilized in the synthesis of such organic π-conjugated materials. In this account, we summarize investigations of the FeCl3-promoted cyclization reaction, the construction of a series of polycyclic aromatics through this method, and the applications of such compounds in thin-film transistors and functional nanomaterials and nanodevices. 1 Introduction 2 Synthetic Considerations 3 Sulfur-Containing Heteroarenes for Thin-Film Transistors 4 Large Heteroarenes for Nanomaterials and Nanodevices 5 Summary and Outlook

Potentially bioactive pyrimidine-annulated spiroheterocyclic compounds are synthesized in good to excellent yields using readily available, cheap and environmentally friendly iron(III) chloride (FeCl3) as the catalyst. The process is straightforward and provides a diverse range of spiropyrimidine derivatives via the 5-endo-dig mode of cyclization, starting from simple and easily available starting materials.

The iron(III) chloride promoted desulfitative C–C coupling of α-oxo ketene dithioacetals with indoles was developed for the synthesis of indole derivatives. In the presence of iron(III) chloride, α-oxo ketene dithioacetals reacted efficiently and highly selectively with C2-unsubstituted or C2-substituted indoles to afford excellent yields of β,β-bisindolyl or β-indolyl α,β-unsaturated carbonyl compounds, respectively.

For the first time Baylis―Hillman adducts derived from nitroolefins have been conveniently transformed into a novel class of building blocks, 1-[(E)-3-bromo-2-nitroprop-1-enyl]arenes and 1-[(E)-3-chloro-2-nitroprop-1-enyl]arenes, in very good yields via an S N 2 reaction using simple reaction conditions. Further application of these compounds has been demonstrated for the synthesis of tris[(E)-2-nitro-3-arylallyl]amines as dendrimer cores.

A new efficient and simple route for the synthesis of 8,9-dihydro-3 H-pyrano[3,2- F]quinoline-3,10(7 H)-dione derivatives has been accomplishedvia sulfuric acid promoted condensation--cyclizationof 6-amino-5-[(trimethylsilyl)ethynyl]-2 H-chromen-2-one and aromatic aldehydes.The products can be oxidized to the corresponding 10-methoxy-8-aryl-3 H-pyrano[3,2- F]quinolin-3-one derivativesby FeCl 3 ˙6H 2 O in methanol.

An efficient method has been developed for the synthesis of Garcia Gonzalez polyhydroxyalkyl- and C-glycosylfurans in excellent yields from unprotected sugar aldoses with β-keto esters by Knoevenagel condensation in the presence of anhydrous iron(III) chloride.

The direct sulfenylation of indoles with aromatic thiols has been accomplished in the presence of 20 mol% of FeCl 3 in refluxing acetonitrile to produce 3-arylthioindoles in relatively good to excellent yields and with high selectivity. This method works even with 2-unsubstituted indoles.

National Natural Science Foundation of China [20772098, 30572250]; Fujian Province University

A new protocol for the β-sulfonation of α,β-unsaturated carbonyl compounds is described. The method employs FeCl 3 as catalyst and TMSCl as additive for conjugate addition of sodium p-toluenesulfinate to enones.

A simple and efficient method for the α-thiocyanation of ketones has been developed; anhydrous iron(III) chloride is used under mild conditions to produce α-oxo thiocyanates in good to high yields and with high selectivity. The use of inexpensive and readily available iron(III) chloride makes this procedure simple, convenient, and practical.

The Nazarov cyclization of silicon-free 3-substituted thiophene derivatives was effectively catalyzed by 10 mol% FeCl 3 , which provided the desired cyclized TRANS product in good yield.

A novel and efficient strategy for the C-acetylation of Baylis-Hillman adducts has been described. Promoted by Sm(0)/Ac 2 O/FeCl 3 /I 2 , the present method allows for the efficient con-version of Morita-Baylis-Hillman adducts to their corresponding 2-alkylidene-4-oxoalkanoate derivatives and reduction products.