Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

• Shao-Cong Zhan,
• Ren-Jie Fang,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

• -arylidene-1,3-dimethylbarbituric acid and 4-methylbenzaldehyde under the standard reaction conditions and further oxidation with DDQ generated the final aromatized product 3a in 75% yield. Under the same reaction conditions, similar aromatized products 3b and 3c were also produced in good yields with

• . On the other hand, the tetrahydrospiro[carbazole-3,5'-pyrimidine] 4 can be converted to aromatized spiro[carbazole-3,5'-pyrimidine] 3 through the oxidation of DDQ. In the absence of the effective dienophile, the normal Friedel–Crafts alkylation of 2-methylindole with aromatic aldehyde gives the well

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

• Durbis J. Castillo-Pazos,
• Juan D. Lasso and
• Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

• halogenation reactions or oxidation. For these reasons, it would be ideal to develop an efficient methodology that allows for the generation of perfluoroalkyl radicals in a mild, redox- and pH-neutral manner, without the assistance of external photocatalysts, heavy metal catalysts, or further additives. Thus

• generated in situ from propiophenone, and second, the deprotection of propiophenone α-thioesters in the presence of perfluoroalkyliodides and subsequent oxidation of the formed perfluorothioether into the sulfone. However, none of these proposed pathways gave yields high enough for the reaction to be

Synthesis of odorants in flow and their applications in perfumery

• Merlin Kleoff,
• Paul Kiler and
• Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

• be extracted from grapefruits or prepared by, e.g., oxidation of (+)-valencene (7) (using toxic di-tert-butyl chromates), which is isolated from the essential oil of oranges [9]. In 2014, Neuenschwander and Jensen reported a flow setup for the catalyst and solvent-free oxidation of (+)-valencene (7

• odor”. Alternatively, the reaction mixture is pumped to an oxidation module in which the pinacol boronates are mixed with a solution of sodium perborate in water/tetrahydrofuran to perform oxidation to the corresponding alcohols 20 at 40 °C in 60 s. In order to quench remaining oxidants, the reaction

• resembling that of hawthorn or a harsh orange-blossom type“. Acetophenone appears in vintage Geoffrey Beene: Grey Flannel at 0.14%, and Shiseido: Zen and Gap: Om at approx. 0.014%. In 2013, Roberge, Kappe, and co-workers investigated the C–H oxidation of ethylbenzene (37) to acetophenone with oxygen as an

Structural basis for endoperoxide-forming oxygenases

• Takahiro Mori and
• Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

• product. The functional analysis of FtmOx1 indicated that the enzyme accepts fumitremorgin B as a substrate and catalyzes the formation of verruculogen and a C13-oxo product, through the installation of an endoperoxide bridge between C21 and C27 of fumitremorgin B and oxidation of the C13-hydroxy group of

• endoperoxide with a C26 radical intermediate. Finally, the radical is quenched by hydrogen atom donation from Tyr224, to form verruculogen and a tyrosyl radical for the next round of the reaction. The tyrosyl radical at Tyr224 is also involved in the oxidation of the C13-hydroxy group of verruculogen to a C13

• -based genome mining approach. While it is possible that many endoperoxide compounds are produced through non-enzymatic oxidation by ROS, future biosynthetic analyses of endoperoxide natural products will lead to the discovery of novel endoperoxide-forming pathways and generate more comprehensive

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• , they are less common due to their inherent toxicity and ease of oxidation. Another branch of research involving SPIONs focuses on developments in nanoscience, nanomedicine, and nanoparticle-assisted imaging, diagnosis, and drug delivery [4][5][6][7], an area that is not covered in this report. Review 1

• continuous process could be established by oxidation with molecular oxygen introduced into the reaction stream via a tube-in-tube membrane reactor, a process which should be very attractive for industrial applications, as oxygen or air act as cheap and environmentally friendly oxidants [82]. An interesting

Rapid gas–liquid reaction in flow. Continuous synthesis and production of cyclohexene oxide

• Kyoko Mandai,
• Tetsuya Yamamoto,
• Hiroki Mandai and
• Aiichiro Nagaki

Beilstein J. Org. Chem. 2022, 18, 660–668, doi:10.3762/bjoc.18.67

• oxidation, a combination of molecular oxygen and aldehydes as a sacrificial agent has been widely studied [9]. However, in general, such a reaction in batch is slow due to the difficulties of performing a gas–liquid reaction in a batch reactor [10]. In addition, even valuable catalysts could not accelerate

• system using oxidants other than air [28][29][30] encouraged us to develop a highly productive flow system with air. Herein, we report that rapid gas–liquid oxidation of cyclohexene with air in the presence of isobutyraldehyde as a sacrificial agent to synthesize cyclohexene oxide is successfully

• achieved by using a flow technique (Scheme 1). Cyclohexene oxide was selectively produced with high yield in our flow oxidation system using air and within only 1.4 min. The fast epoxidation of cyclohexene without added catalyst in the solution was achieved since the solution of cyclohexene and aldehyde in

DDQ in mechanochemical C–N coupling reactions

• Shyamal Kanti Bera,
• Rosalin Bhanja and
• Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

• obtained in 88% yield (Table 1, entry 1). However, in the presence of 1.2 equiv, the yield of 2a increased to 97% (Table 1, entry 2). Further, with the increase of the amount of DDQ to 1.5 equiv, no further improvement was obtained (Table 1, entry 3). In addition, we have screened several iodine oxidation

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• using triethylamine as base to give the corresponding 3-thiopyrazoles 9a–e in moderate yields (28–69%). By oxidation of sulfane 9d with m-chloroperbenzoic acid in chloroform at room temperature the sulfoxide 10d was obtained in 43% yield (Scheme 7). For comparing the biological activity of the newly

• . Interestingly, the oxidation of the sulfur atom in pyrazole 9d (EC50 = 1.1 ± 0.04 µM) improved the antimalarial activity by a factor of more than three (sulfoxide 10d, EC50 = 0.3 ± 0.01 µM). In our experiments we used the established antimalarial drug amodiaquine as control. As shown in Table 1, the EC50 of

• synthetic building block 2-nitroperchlorobutadiene (1). 3-(Alkyl)(2-hydroxyethyl)aminopyrazoles 7 are accessible from the reaction of oxazolidine derivative 6 with 7-chloro-4-hydrazinylquinoline. Oxidation of sulfane 9d led to the formation of the pharmacologically interesting sulfoxide 10d. The newly

BINOL as a chiral element in mechanically interlocked molecules

• Matthias Krajnc and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

• (DMDO) was used to obtain the corresponding amine N-oxides (R,R/S)-30a–f in 80–99% yield. This oxidation takes place inside the chiral macrocycle, so that the resulting stereogenic nitrogen is formed in a diastereoselective fashion. Interestingly, for rotaxanes (R,R/S)-30a–c, which feature C3/C6/C12

• . Synthesis of Stoddart´s BINOL-containing [2]catenanes 18/20/22/24 by π–π recognition. Synthesis of Takata´s rotaxanes featuring chiral centers on the axle: a) rotaxane (R,R,R/S)-27 obtained by thiol–ene addition and b) rotaxanes (R,R/S)-30a–f obtained by amine oxidation. Takata´s chiral polyacetylenes 32/33

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• methylsulfonyl group was necessary to perform. A suitable oxidant for this purpose appeared to be oxone [40]. Thus, the oxidation of tCbz-mPYR with oxone proceeded in DMF at 80 °C to provide the 2-methylsulfonyl derivative 3 in 92% yield. Then, treatment of compound 3 with NaCN or 4-(tert-butyl)thiophenol led to

• pyrimidine–carbazole TADF emitters bearing different substituents in position 2 of the pyrimidine moiety were successfully prepared by using Liebeskind–Srogl cross-coupling, hydrogenolysis, oxidation reactions of 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methyl-2-methylthiopyrimidine and following

Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• dispirocyclopentanebisoxindoles from two molecules of 3-phenacylideneoxindoles, accomplished by reduction of one molecule of 3-phenacylideneoxindole by thiol [24]. In 2017, Thennarasu et al. [25] reported the tandem oxidation/Michel-aldol reaction of 3-phenacyloxindoles for the synthesis of dispirocycliopentanebisoxindoles

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• , followed by oxidation, thus establishing a redox cycle. The main characteristics of the quinones (Q) redox cycle, comprises the one-electron reduction to generate a semiquinone intermediate (SQ) and the two-electron reduction leading to hydroquinone (HQ), in NAD(P)H oxidase-dependent processes [35][36][37

• . Review Preparation methods of menadione Among the most common methods for the preparation of menadione (10), we can find, for example, the oxidation of 2-methylnaphthalene or 2-methylnaphthol. Other less frequent but equally efficient approaches to synthesize menadione include the demethylation of 2

• menadione. Oxidation of 2-methylnaphthalene Menadione synthesis through the oxidation of 2-methylnaphthalene (16) includes the use of oxygen-rich oxidants using various reaction conditions and a broad range of well-succeeding methodologies has been reported. A summary is presented in Table 1 and will be

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• the end product of the pathway in N. altamirensis DSM 44997. Previous studies have demonstrated that, in nature, hydroxamates arise from the oxidation of terminal amino groups in amino acid side chains, followed by formylation or acylation of the resulting hydroxylamines. While the oxidations are

• catalyzed by flavin-dependent monooxygenases [12][13][14][15][16], the carbon transfer is mediated either by tetrahydrofolate-dependent formyl [17] or by acyl-CoA-dependent acyl transferases [13][15][16]. It is widely assumed that the oxidation precedes the formylation or acylation [17][18][19][20][21][22

Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

• Yuki Naito,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

• and sustainable synthetic method in the face of increasingly stringent environmental and economic constraints. In this context, several groups have demonstrated the electrochemical synthesis of piperidine and pyrrolidine derivatives by anodic oxidation [22][23][24][25][26]. In contrast, there has been

• time, extremely fast molecular diffusion, and expelling the reaction product to avoid over-oxidation or over-reduction. We have previously reported the electrochemical carboxylation of several imines in a flow microreactor to afford the corresponding α-amino acids in good to moderate yields [33][34][35

• electrodes and subjected to the electrolytic reaction. Tetrahydrofuran (THF), which is easily oxidized, was employed as the electrolytic solvent, so the reaction at the anode (counter electrode) is thought to be preferentially caused by the oxidative decomposition of THF, and the re-oxidation of the cathodic

Site-selective reactions mediated by molecular containers

• Rui Wang and
• Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

• , azides, halides and alkenes, oxidation of remote C–H bonds and alkenes, and substitution reactions involving ring-opening cyclization of epoxides, nucleophilic substitution of allylic chlorides, and hydrolysis reactions. The product selectivity is interpreted as the consequence of the space shape and

• , that is, selective reactions that take place at one specific potential reactive site out of the similar others, in this review. In the following part, the literature reports will be mainly divided according to the reaction types, namely cycloaddition/addition, reduction, oxidation, and substitution

• powerful role of molecular containers to achieve precise transformation of complex molecules. Oxidation C–H bonds are ubiquitously distributed in nearly all of the organic compounds, which makes them predominant candidates for the modification of complex molecules. Without pre-activation, direct

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• of Fe3+ ions into the solution directly interacts with the nitrogen atom of the hexaphenylbenzene (HPB)-based derivative and reduces the oxidation state from Fe(III) to Fe(0) which is further oxidized by the aqueous medium. Hence the aggregates of HPB can act as a good stabilizing agent. Similarly

• aqueous medium under aerobic conditions (Scheme 26) [39]. The graphene support was prepared by oxidation of graphite, treatment of the resulting graphene oxide with ethylene diamine in an autoclave followed by freeze-drying to obtain three dimensional graphene with a high nitrogen content. Heating of the

• glycol groups. In addition, the aryl halide oxidatively adds to copper changing its oxidation state to +3. Finally, the desired product is formed by reductive elimination and the catalyst returns to the cycle (Scheme 33). The designed catalyst was characterized by different techniques which showed

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• , Ural Federal University named after the first President of Russia B. N. Yeltsin, Mira str. 19, Yekaterinburg, 620002, Russian Federation 10.3762/bjoc.18.29 Abstract A series of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines has been synthesized through oxidation reaction of the corresponding 3,6

• can also be used as an oxidant for the oxidation of benzamidine derivatives 2b,c in acetonitrile under microwave irradiation. Along with the cyclization reaction, bromination of the pyrazole ring proved to occur at position C(4) to give the products 3j,k, as evidenced by disappearance of the

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• , including amlodipine and nifedipine [24]. The structure of 1,4-DHP resembles the coenzyme NADH, which is very important in oxidation and reduction reactions in biological systems. 4-Substituted 1,4-DHPs have been used in the treatment of cardiovascular diseases as organic calcium channel modulators [25

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• -en-10-one is described. cis-9-Azabicyclo[6.2.0]dec-6-en-10-one was transformed into the corresponding amino ester and its protected amine. Oxidation of the double bond in the N-Boc-protected methyl 2-aminocyclooct-3-ene-1-carboxylate then delivered the targeted amino acid and its derivatives. Density

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• -4-sulfonic acid (15) by oxidation with nitric acid in an aqueous medium (Scheme 1A). In 1894, Böniger developed [44] the first reaction of β-NQS with phenylamines. He synthesized β-NQS using a modified method developed by Witt, which quickly reacted with different amines to form colored products

• transformed into α-nitroso-β-naphthol (17); then, in a single step, a sulfonic group was added, and the nitrous group was reduced, forming compound 15, which was transformed into β-NQSNa (18) after oxidation with nitric acid. Despite not knowing exactly the structure of the adduct, Folin speculated that the

• -naphthoquinones 35 and β-lapachone (11) for hCE1 (Scheme 9). It is important to note that 35 can be obtained from other reagents, such as 2-naphthol, in a cascade of reactions involving oxidation to 1,2-naphthoquinones followed by Michael addition to the olefin and reoxidation [85]. In addition, Yang and co

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

• Thaipparambil Aneeja,
• Cheriya Mukkolakkal Abdulla Afsina,
• Padinjare Veetil Saranya and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

• . The ability to exhibit multiple oxidation states increased the demand of ruthenium in the field of catalysis. These cyanation reactions have wide application in pharmacological and biological fields. This review gives an overview of the ruthenium-catalyzed cyanation reactions covering literature up to

• . Commonly used metallic cyanating agents include K4Fe(CN)6, CuCN, KCN, NaCN, TMSCN etc. Ruthenium-catalyzed reactions have gained significant attention in recent times [26]. Ruthenium has the ability to show a large number of oxidation states, and thus a large number of complexes can be prepared using this

• cyclic amines than the aerobic oxidation system. The catalytic cycle for the hydrogen peroxide system involves the formation of the oxoruthenium species (A) and the low-valent ruthenium species (B), whereas the aerobic oxidation system includes C–H activation and a subsequent reaction with molecular

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• macrocyclisation product, which was confirmed by MALDI-ToF-MS of the crude reaction mixture after test cleavage (see Supporting Information File 1, Figure S1). However, deboronation and dehalogenation were observed as side reactions to some extent as well as oxidation, most likely of methionine (Met) [79]. The

• oxidation could be minimised by improved cleavage conditions under argon. Replacing sSPhos by tri(o-tolyl)phosphine (P(o-Tol)3), that had successfully been applied for peptide cyclisation by on-resin SMC [78][80], led to incomplete conversion. The cyclisation of the same peptide with the regioisomer 6

DABCO-promoted photocatalytic C–H functionalization of aldehydes

• Bruno Maia da Silva Santos,
• Mariana dos Santos Dupim,
• Cauê Paula de Souza,
• Thiago Messias Cardozo and
• Fernanda Gadini Finelli

Beilstein J. Org. Chem. 2021, 17, 2959–2967, doi:10.3762/bjoc.17.205

• -electron oxidation of DABCO into its radical cation, the active species responsible for HAT activation of the aldehyde. Our results showed that intermediate amounts of DABCO (0.5 equiv) led to the best results (Table 1, entries 2 and 5; see Supporting Information File 1, Table S1 for details). Unexpectedly

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• as the electrolyte and Fc/Fc+ as the internal reference, data are reported versus a saturated calomel electrode (SCE). In both DICzTRZ and ICzTRZ [14] we observed a reversible oxidation wave with respective oxidation potential (Eox) at 0.87 V and 0.96 V vs SCE (Figure 4a). Both compounds also present

• a second oxidation wave that is more prominent and cathodically shifted for DICzTRZ at 1.05 V, compared to 1.14 V for ICzTRZ. No reduction wave is observed for DICzTRZ. The HOMO value calculated from the oxidation potential obtained from differential pulse voltammetry (DPV), is −5.21 eV, which is

• stabilized compared to that predicted from DFT (EHOMO: −5.03 eV); however, the less positive oxidation potentials in DICzTRZ versus ICzTRZ does align with the predictions obtained by DFT. The UV–vis absorption spectrum of DICzTRZ, while slightly red-shifted and with higher molar absorptivity (as was the case

Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• to the late TMs, iron can possess a wide array of oxidation states, ranging from 2− to 6+, allowing for iron catalysis to be utilized and perform several different types of reactions. As such, a closer look at Fe-catalyzed cascade reactions reveals several distinct features. One possible method for

• the initiation of a multistep reaction is through the generation of an organoiron species. This can occur by the oxidative insertion of a low-valent iron into a C–X bond (Scheme 2). Evidently, iron in low oxidation states may operate as an iron-centered nucleophile, and catalyze reactions involving

• with the reductive addition or difunctionalization of the π-system; however, it has been demonstrated the radical intermediate can go through a SET oxidation/elimination to recover the initiating π-functionality. In this review, Fe-catalyzed domino coupling reactions involving π-systems will be