Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• functions of B12 are exploited by bound apoenzymes. B12 is recycled or reactivated in vivo as observed in methyonine synthetases. Understanding the mechanisms of B12 enzyme reactions and the role of B12 is very important from the viewpoint of bioinorganic and organometallic chemistry, organic syntheses, and

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

• Henrike Ehrhorn,
• Janin Schlösser,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

• , MMPO = 1-methoxy-2-methylpropan-2-ol) was isolated which catalyzed alkyne metathesis of 1-heptyne at elevated temperatures [68] and to date represents the only well-defined ditungsten complex which has been successfully used in alkyne metathesis. The organometallic chemistry of the M2X6 complexes (X

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• ]. With regard to this the high relevance of London dispersion type interactions in molecular organometallic chemistry was recently summarized by Liptrot and Power [9]. It should be noted that in this context and more generally organometallic bismuth compounds are witnessing growing attention since

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• Xiang Li Pinhong Chen Guosheng Liu State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China 10.3762/bjoc.14.154 Abstract Hypervalent iodine(III

Main group mechanochemistry

• Agota A. Gečiauskaitė and
• Felipe García

Beilstein J. Org. Chem. 2017, 13, 2068–2077, doi:10.3762/bjoc.13.204

• . In the field of organometallic chemistry, we highlight the large-scale synthesis of SrCp′2(OEt2) (Cp′ = C5Me4(n-Pr)) (1) [82], an ideal precursor for the chemical vapour deposition (CVD) of strontium-based semiconductors – a key material in memory devices [83]. Previously, this compound could only be

Green chemistry

• Luigi Vaccaro

Beilstein J. Org. Chem. 2016, 12, 2763–2765, doi:10.3762/bjoc.12.273

• , including “Strategies in asymmetric catalysis” by Tehshik P. Yoon [6], “Organometallic chemistry” by Bernd F. Straub and Lutz H. Gade [7], “C–H functionalization/activation in organic synthesis” by Richmond Sarpong [8], “Bifunctional catalysis” by Darren J. Dixon [9], “Sustainable catalysis” by Nicholas J

Protonated paramagnetic redox forms of di-o-quinone bridged with p-phenylene-extended TTF: A EPR spectroscopy study

• Nikolay O. Chalkov,
• Vladimir K. Cherkasov,
• Gleb A. Abakumov,
• Andrey G. Starikov and
• Viacheslav A. Kuropatov

Beilstein J. Org. Chem. 2016, 12, 2450–2456, doi:10.3762/bjoc.12.238

• Nikolay O. Chalkov Vladimir K. Cherkasov Gleb A. Abakumov Andrey G. Starikov Viacheslav A. Kuropatov Laboratory of Organoelement Compounds, G.A. Razuvaev Institute of Organometallic Chemistry of RAS, 603950, GSP-445, Tropinina str., 49, Nizhny Novgorod, Russia N. I. Lobachevsky Nizhny Novgorod

Organometallic chemistry

• Bernd F. Straub,
• Rolf Gleiter,
• Claudia Meier and
• Lutz H. Gade

Beilstein J. Org. Chem. 2016, 12, 2216–2221, doi:10.3762/bjoc.12.213

• -Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany 10.3762/bjoc.12.213 This Thematic Series is dedicated to the memory of Professor Peter Hofmann (Figure 1) whose research work included many seminal contributions to the field of organometallic chemistry [1][2

• ][3]. Organometallic chemistry has therefore been chosen as the topic of this Thematic Series of the Beilstein Journal of Organic Chemistry. Over a period of many decades, the chemistry of metal–carbon bonds has given rise to an ever-growing field of fundamental research and applied science, merging

• organometallic chemistry in its own right, but also demonstrate the vital role that research in organometallic chemistry plays as a provider of invaluable tools for other chemistry sub-disciplines. We thank the authors for their excellent contributions and are grateful for the commitment and the support of the

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• toward biology. On to graduate school in organometallic chemistry Once I “found” organic chemistry, the path to graduate school was relatively direct. My TA, Rich Engler, encouraged me to pursue research, and I did so, joining the group of Professor Perrin, who had engaged me in organic chemistry in the

• education! With my research experiences in physical organic chemistry and inorganic chemistry, and with the boom in organometallic research at that time, I chose to pursue mechanistic organometallic chemistry for my Ph.D. at the University of Chicago in the group of Bill Wulff. Research in the group spanned

• Dennis Dougherty’s work on cation–π interactions (Figure 3a) [2]. Thus, while at the time I was intent on studying organometallic chemistry, my interest in supramolecular chemistry increased the more I read through graduate school, and particularly molecular recognition in aqueous solution, which I

Cp₂TiCl/D₂O/Mn, a formidable reagent for the deuteration of organic compounds

• Antonio Rosales and
• Ignacio Rodríguez-García

Beilstein J. Org. Chem. 2016, 12, 1585–1589, doi:10.3762/bjoc.12.154

• experimental conditions and with great economic advantages. Keywords: deuteration; deuterium atom transfer; radical and/or organometallic chemistry; titanocene; Introduction Deuterium is a stable isotope of hydrogen with 0.015% natural abundance broadly used in organic chemistry, pharmacology, organometallic

• chemistry, spectroscopy and many other fields [1][2][3][4]. Exchange of hydrogen for deuterium produces primary and secondary kinetic isotope effects (KIE) causing isotopically substituted molecules to react at different rates (kH ≠ kD). This behaviour is due to the differences in bond dissociation energies

Ring-whizzing in polyene-PtL₂ complexes revisited

• Oluwakemi A. Oloba-Whenu,
• Thomas A. Albright and
• Chirine Soubra-Ghaoui

Beilstein J. Org. Chem. 2016, 12, 1410–1420, doi:10.3762/bjoc.12.135

• due to the interaction between b1 (7) and the HOMO on 6-radialene, which is the totally antibonding combination of π orbitals, 27. B. The strange case of cyclooctatetraene Cyclooctatetraene (COT) has been a favorite ligand since the dawn of organometallic chemistry [2]. Figure 8 shows two

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• atmosphere at room temperature. Keywords: copper; CuAAC reaction; : N-heterocylic carbene; 1,2,3-triazole; Introduction N-Heterocyclic carbene (NHC) have interesting electronic and structural properties. This resulted in their use as versatile ligands in organometallic chemistry and homogeneous catalysis

Indenopyrans – synthesis and photoluminescence properties

• Andreea Petronela Diac,
• Ana-Maria Ţepeş,
• Albert Soran,
• Ion Grosu,
• Anamaria Terec,
• Jean Roncali and
• Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

• Andreea Petronela Diac Ana-Maria Tepes Albert Soran Ion Grosu Anamaria Terec Jean Roncali Elena Bogdan Babeş-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry (CSOOMC) Cluj-Napoca, 11 Arany Janos, 400028 Cluj-Napoca, Romania Group Linear Conjugated Systems, CNRS

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• ; iridium; isomerization; N-heterocyclic carbene; rhodium; Introduction In the framework of organometallic chemistry, N-heterocyclic carbenes (NHC) centre a well stablished class of relatively new ligands since in 1991 Arduengo and collaborators isolated the first stable NHC of the imidazole type with

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• dialkyne spacers In the past years, bistriazoles with dialkyne spacers have gained significant attention for their potential application in supramolecular chemistry, pharmaceutical chemistry, biological chemistry and organometallic chemistry. The construction of bistriazoles from dialkynes is now well

Comparison of the catalytic activity for the Suzuki–Miyaura reaction of (η⁵-Cp)Pd(IPr)Cl with (η³-cinnamyl)Pd(IPr)(Cl) and (η³-1-t-Bu-indenyl)Pd(IPr)(Cl)

• Patrick R. Melvin,
• Nilay Hazari,
• Hannah M. C. Lant,
• Ian L. Peczak and
• Hemali P. Shah

Beilstein J. Org. Chem. 2015, 11, 2476–2486, doi:10.3762/bjoc.11.269

• [15]. In particular, precatalysts based on the (η3-1-t-Bu-indenyl)Pd(L)(Cl) scaffold were highly active because Pd(I) dimer formation was effectively suppressed and the rate of reduction from Pd(II) to Pd(0) was increased [16]. In organometallic chemistry, allyl and indenyl ligands are considered to

N-Heterocyclic carbenes

• Steven P. Nolan

Beilstein J. Org. Chem. 2015, 11, 2474–2475, doi:10.3762/bjoc.11.268

• Steven P. Nolan Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia 10.3762/bjoc.11.268 The N-heterocyclic carbenes (NHC) now hold a preferred-ligand status in organic and organometallic chemistry. Their role in catalysis continues to grow. When the

Highly selective palladium–benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions

• Antonio Monopoli,
• Pietro Cotugno,
• Carlo G. Zambonin,
• Francesco Ciminale and
• Angelo Nacci

Beilstein J. Org. Chem. 2015, 11, 994–999, doi:10.3762/bjoc.11.111

• activity is still mandatory in these kind of reactions. Among various ligands, N-heterocyclic carbenes (NHCs) have gained greater importance in organometallic chemistry. Unlike phosphanes, NHCs are not toxic and insensitive to air, heat and moisture. Moreover, the introduction of substituents onto the

An improved procedure for the preparation of Ru(bpz)₃(PF₆)₂ via a high-yielding synthesis of 2,2’-bipyrazine

• Danielle M. Schultz,
• James W. Sawicki and
• Tehshik P. Yoon

Beilstein J. Org. Chem. 2015, 11, 61–65, doi:10.3762/bjoc.11.9

• investigated for a wide range of applications in inorganic and organometallic chemistry [20][21][22][23][24][25]. Unfortunately, the synthesis of 2,2’-bipyrazyl (bpz) is quite challenging compared to the syntheses of other, structurally similar bidentate bisazene ligands. Various methods for the preparation of

One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

• Joshua P. Barham,
• Matthew P. John and
• John A. Murphy

Beilstein J. Org. Chem. 2014, 10, 2981–2988, doi:10.3762/bjoc.10.316

• reasons. Firstly, a virtually limitless host of carbon nucleophiles may be employed via organometallic chemistry (compounds 6aa–6af are novel compounds derived from unstabilised carbon nucleophiles). Secondly, photoredox catalysis can be substrate tailored through photocatalyst selection. Having

Synthesis of 1-[bis(trifluoromethyl)phosphine]-1’-oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates

• Zeng-Wei Lai,
• Rong-Fei Yang,
• Ke-Yin Ye,
• Hongbin Sun and
• Shu-Li You

Beilstein J. Org. Chem. 2014, 10, 1261–1266, doi:10.3762/bjoc.10.126

• Zeng-Wei Lai Rong-Fei Yang Ke-Yin Ye Hongbin Sun Shu-Li You State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China State Key Laboratory of Natural Medicines and Center of Drug Discovery, China

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

• Yin-wei Sun,
• Qin Xu and
• Min Shi

Beilstein J. Org. Chem. 2013, 9, 2224–2232, doi:10.3762/bjoc.9.261

• Yin-wei Sun Qin Xu Min Shi Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, and 130 MeiLong Road, Shanghai 200237, People’s Republic of China, State Key Laboratory of Organometallic

• Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, People’s Republic of China 10.3762/bjoc.9.261 Abstract Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes

Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives

• Yin-wei Sun,
• Qin Xu and
• Min Shi

Beilstein J. Org. Chem. 2013, 9, 1969–1976, doi:10.3762/bjoc.9.233

• Yin-wei Sun Qin Xu Min Shi Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 MeiLong Road, Shanghai 200237, People’s Republic of China, State Key Laboratory of Organometallic

• Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, People’s Republic of China 10.3762/bjoc.9.233 Abstract Oxabicyclic alkenes can react with electron-deficient terminal alkynes in the presence of a gold catalyst under mild conditions

Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes

• Yan-Chao Shi,
• Rong-Fei Yang,
• De-Wei Gao and
• Shu-Li You

Beilstein J. Org. Chem. 2013, 9, 1891–1896, doi:10.3762/bjoc.9.222

• Yan-Chao Shi Rong-Fei Yang De-Wei Gao Shu-Li You State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China Process Development and Manufacturing Department, Pharmaron (Beijing) Co. Ltd., 6 Taihe