Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

• Daria A. Burmistrova,
• Andrey Galustyan,
• Nadezhda P. Pomortseva,
• Kristina D. Pashaeva,
• Maxim V. Arsenyev,
• Oleg P. Demidov,
• Mikhail A. Kiskin,
• Andrey I. Poddel’sky,
• Nadezhda T. Berberova and
• Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

• , Russia G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Tropinin str. 49, 603137, Nizhny Novgorod, Russia North-Caucasus Federal University, Pushkin str. 1, 355017, Stavropol, Russia Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• recent achievements on the synthesis and functionalization of indole derivatives via carbonylative approaches. Keywords: carbonylation; functionalization; indole; metal catalyst; organometallic chemistry; Introduction Indole is a heterocyclic compound consisting of a benzene ring fused with a pyrrole

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• just three decades (Figure 1) [2]. In particular, cyclic diaminocarbenes based on the imidazoline, benzimidazole, or imidazole ring system (A–C) have led to a myriad of applications in organometallic chemistry, homogeneous catalysis, and materials science, to name just a few [3][4][5]. Due to their

Active-metal template clipping synthesis of novel [2]rotaxanes

• Cătălin C. Anghel,
• Teodor A. Cucuiet,
• Niculina D. Hădade and
• Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

• Catalin C. Anghel Teodor A. Cucuiet Niculina D. Hadade Ion Grosu Babeș-Bolyai University, Faculty of Chemistry and Chemical Engineering, Supramolecular Organic and Organometallic Chemistry Centre, 11 Arany Janos Str., RO-400028-Cluj-Napoca, Romania University of Bucharest, Faculty of Chemistry

C–H bond functionalization: recent discoveries and future directions

• Indranil Chatterjee

Beilstein J. Org. Chem. 2023, 19, 1568–1569, doi:10.3762/bjoc.19.114

• its combination with organometallic chemistry for site-selective C−H bond functionalization [3][4]. Recent years have witnessed many viable strategies for the synthesis of complex targets utilizing photoredox catalysis, electroorganic catalysis, Lewis acid catalysis, and transition-metal-free

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• caused by its structural features. NHCs constitute a well-established class of new ligands in organometallic chemistry. Although initially NHCs were regarded as pure σ-donor ligands, later experimental and theoretical studies established the presence of a significant back donation from the d-orbital of

• ligands in organometallic chemistry. After the first synthesis of stable monomeric NHCs, spectroscopic studies promptly revealed their similarity with phosphines. Indeed, both these classes of ligands are σ-donor ligands with low π-backdonating character [16][17]. In the beginning, the NHCs were perceived

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

• bond of 105 provides a seven-membered rhodacyclic intermediate 106. The protonation at the Rh–C bond of intermediate 106 in the presence of RCOOH furnishes hydroarylation product 104. Nitrogen heterocyclic carbenes (NHCs) are of central importance in organometallic chemistry and in organic synthesis

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

• -stage transition metals have contributed immensely to synthetic organic and organometallic chemistry, increasing societal awareness in terms of sustainable developments and resource management has prompted chemists to explore the use of environmentally benign, inexpensive, and earth-abundant metals [18

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

• perfluorinated chains into aromatic rings have been developed since the first reports of such transformation by George Tiers in 1960, and McLoughlin and Thrower in 1969 [2][3]. Most approaches have made extensive use of organometallic chemistry, radical initiators, photocatalysis, electrochemistry, and more

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

• 400 °C exposed to an air flow. The importance of this study is the fact that no activating agents are required and water is the only byproduct. Organometallic chemistry and heating are not among the most intuitively sensible combinations. However, prior to the formation of an organometallic species

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

• ], nickel [20][21][22][23], and iridium [24][25][26][27] have taken center stage when it comes to the development of synthetic methodology. Although these late TMs have contributed enormously to the various fields of organic, inorganic, and organometallic chemistry, growing concerns regarding their economic

Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

• Tülay Yıldız,
• İrem Baştaş and
• Hatice Başpınar Küçük

Beilstein J. Org. Chem. 2021, 17, 2203–2208, doi:10.3762/bjoc.17.142

• organometallic chemistry and using transition metal catalysts, which need expensive and toxic chemicals. With the increasing interest in these methods, new organocatalysts and reagents that are less toxic, easier to use, readily accessible, and cheap have been developed [37]. In particular, the synthesis of

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• organometallic chemistry and catalysis [128]. The first example of a stoichiometric manganese-mediated C–H activation, reported by Stone, Bruce, and co-workers (1970) [129], was an ortho-metalation in azobenzenes. In recent years, with the expansion of the C–H activation field, manganese catalysts have been

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

• Anthony J. Fernandes,
• Armen Panossian,
• Bastien Michelet,
• Agnès Martin-Mingot,
• Frédéric R. Leroux and
• Sébastien Thibaudeau

Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32

• beneficial effects generally resulting from the introduction of these fluorinated motifs [13], also participated in this development. These fluorine effects are nowadays remarkably established in many domains, including medicinal, organic, and organometallic chemistry, catalysis, chemical biology, and

Annulation of a 1,3-dithiole ring to a sterically hindered o-quinone core. Novel ditopic redox-active ligands

• Sergey V. Norkov,
• Anton V. Cherkasov,
• Andrey S. Shavyrin,
• Maxim V. Arsenyev,
• Viacheslav A. Kuropatov and
• Vladimir K. Cherkasov

Beilstein J. Org. Chem. 2021, 17, 273–282, doi:10.3762/bjoc.17.26

• Sergey V. Norkov Anton V. Cherkasov Andrey S. Shavyrin Maxim V. Arsenyev Viacheslav A. Kuropatov Vladimir K. Cherkasov G. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Tropinina str. 49, Box-445, 603950 Nizhny Novgorod, Russia N. I. Lobachevsky Nizhny Novgorod

Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes

• Yajing Zhang,
• Qingshan Tian,
• Guozhu Zhang and
• Dayong Zhang

Beilstein J. Org. Chem. 2020, 16, 3086–3092, doi:10.3762/bjoc.16.258

• Yajing Zhang Qingshan Tian Guozhu Zhang Dayong Zhang School of Science, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210000, P. R. China State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai

• intermediate to synthesize a β-fluorovinylphosphonate. Optimization of the reaction conditions. Supporting Information Supporting Information File 486: Experimental procedures, full characterization of products, and NMR spectra. Funding We are grateful to NSFC-21772218, State Key Laboratory of Organometallic

• Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences for financial support.

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• palladium(II) was carried out in the presence of PdCl2(MeCN)2 in a stepwise manner, confirmed by UV–vis spectroscopic technique. The cyclopentadienyl (Cp) ligand has its own identity in the field of organometallic chemistry as a plethora of transition metal complexes contain this moiety in their structures

Efficient [(NHC)Au(NTf₂)]-catalyzed hydrohydrazidation of terminal and internal alkynes

• Maximillian Heidrich and
• Herbert Plenio

Beilstein J. Org. Chem. 2020, 16, 2080–2086, doi:10.3762/bjoc.16.175

• Maximillian Heidrich Herbert Plenio Organometallic Chemistry, Technische Universität Darmstadt, Alarich-Weiss-Str. 12, 64287 Darmstadt, Germany 10.3762/bjoc.16.175 Abstract The efficient hydrohydrazidation of terminal (6a–r, 18 examples, 0.1–0.2 mol % [(NHC)Au(NTf2)], T = 60 °C) and internal

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry. Keywords: Knochel–Hauser base; lithium chloride; magnesium; on-demand; packed-bed reactors; plug and flow reactor; synthesizer; turbo Grignard reagent

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• possibilities: two different competitive C=C bonds amenable to undergo photocycloaddition and at least three different C–H bonds that can be activated by a transition metal provide the potential for a rich organic and organometallic chemistry. Moreover, both the arylidene and the styryl groups can be tuned with

• Esteban P. Urriolabeitia Pablo Sanchez Alexandra Pop Cristian Silvestru Eduardo Laga Ana I. Jimenez Carlos Cativiela Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, Spain Supramolecular Organic and Organometallic

• Chemistry Centre, Departament of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Str. Arany Janos 11, RO-400028 Cluj−Napoca, Romania 10.3762/bjoc.16.98 Abstract The stereoselective synthesis of truxillic bis-amino esters from polyfunctional oxazolones is reported. The

Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

• Zhenghui Liu,
• Peng Wang,
• Zhenzhong Yan,
• Suqing Chen,
• Dongkun Yu,
• Xinhui Zhao and
• Tiancheng Mu

Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61

• friendly and highly effective synthetic methods has been a significant goal of research [1][2][3][4][5]. In this aspect, effective catalytic systems and organometallic chemistry are suitable technologies to accomplish these goals. Carbonylation processes are important transformations in the refinement and

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• -heterocyclic phosphines; Introduction Phosphines constitute a large percentage of ligands in organometallic chemistry and over the years, they have received enormous attention. The main interest towards this class of compounds is attributed to aspects such as, the good electron-donating ability of the

• (NHCs) have proved to be versatile ligands in organometallic chemistry [82]. The synthesis of sterically crowded biaryl ligands is still a challenging task, especially under mild reaction conditions. The diphosphine complexes of imidazolylphosphines proved to be an alternative towards the coupling of

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• properties, synthetic transformations, organometallic chemistry and metal-catalysed reactions, an excellent review was recently published by Radhakrishnan and co-workers [33]. This highlight article is intended to give the reader an overview of the varied and exceptional cycloaddition chemistry of fulvenes

Halide metathesis in overdrive: mechanochemical synthesis of a heterometallic group 1 allyl complex

• Ross F. Koby,
• Nicholas R. Rightmire,
• Nathan D. Schley,
• Timothy P. Hanusa and
• William W. Brennessel

Beilstein J. Org. Chem. 2019, 15, 1856–1863, doi:10.3762/bjoc.15.181

• ; metathesis; potassium; Introduction Halide (or ‘salt’) metathesis is a broadly useful synthetic technique in organometallic chemistry, applicable to elements across the entire periodic table. A typical instance involves the reaction of a metal halide (M'Xn) with an organoalkali metal compound (RM; M = Li

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

• dimethylamino- or nitro-substituted aldehydes did not result in the target compound that might be due to the deactivation caused by coordination of these groups with the catalyst. Metal–carbene complexes attracted the attention of organic chemists and have become an important branch of organometallic chemistry