Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

• Youlong Du,
• Haibo Mei,
• Ata Makarem,
• Ramin Javahershenas,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

• Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country (UPV/EHU), Paseo Manuel Lardizábal 3, San Sebastián, 20018, Spain

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• Anna V. Orlova Nelly N. Malysheva Maria V. Panova Nikita M. Podvalnyy Michael G. Medvedev Leonid O. Kononov Laboratory of Glycochemistry, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation Theoretical Chemistry Group, N.D. Zelinsky Institute of Organic Chemistry, Moscow

NMRium: Teaching nuclear magnetic resonance spectra interpretation in an online platform

• Luc Patiny,
• Hamed Musallam,
• Alejandro Bolaños,
• Michaël Zasso,
• Julien Wist,
• Metin Karayilan,
• Eva Ziegler,
• Johannes C. Liermann and
• Nils E. Schlörer

Beilstein J. Org. Chem. 2024, 20, 25–31, doi:10.3762/bjoc.20.4

• and published in the area of organic chemistry has been almost unchanged over the last five decades, in spite of tremendous experimental progress [1]. Only in specialized (sub)disciplines of NMR (e.g., biomolecular and metabolomic applications), adequate handling of spectral data has been adapted or

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• Pavel S. Silaichev Tetyana V. Beryozkina Vsevolod V. Melekhin Valeriy O. Filimonov Andrey N. Maslivets Vladimir G. Ilkin Wim Dehaen Vasiliy A. Bakulev Department of Organic Chemistry, Perm State University, 15 Bukireva st., Perm 614990, Russia TOS Department, Ural Federal University, 19 Mira st

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF₃: the case of alkyne hydration. Chemistry vs electrochemistry

• Marta David,
• Elisa Galli,
• Richard C. D. Brown,
• Marta Feroci,
• Fabrizio Vetica and
• Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

• complex organic compounds, widely used both in organic chemistry and in electrochemistry as raw materials for the preparation of different molecules of pharmaceutical and industrial interest [1][2][3][4][5][6][7][8][9]. Among the different organic transformations involving alkynes, their hydration is a

• well-known and useful reaction in organic chemistry, affording carbonyl compounds based on an atom-economical approach. Indeed, the addition of water to the triple bond of a terminal alkyne leads to the formation of the corresponding methyl ketone or aldehyde, in the case of Markovnikov or anti

• identification of new catalysts as well as increasingly mild, economic and sustainable reaction conditions remain fundamental objectives for research in the field of organic chemistry. In recent years, alternative methods have been developed, including the use of different heterogeneous catalysts, to ensure

Anion–π catalysis on carbon allotropes

• M. Ángeles Gutiérrez López,
• Mei-Ling Tan,
• Giacomo Renno,
• Augustina Jozeliūnaitė,
• J. Jonathan Nué-Martinez,
• Javier Lopez-Andarias,
• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2023, 19, 1881–1894, doi:10.3762/bjoc.19.140

• M. Angeles Gutierrez Lopez Mei-Ling Tan Giacomo Renno Augustina Jozeliunaite J. Jonathan Nue-Martinez Javier Lopez-Andarias Naomi Sakai Stefan Matile Department of Organic Chemistry, University of Geneva, Geneva, Switzerland 10.3762/bjoc.19.140 Abstract Anion–π catalysis, introduced in 2013

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• Gyula Dargo Dora Erdelyi Balazs Molnar Peter Kisszekelyi Zsofia Garadi Jozsef Kupai Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary Department of Pharmacognosy, Semmelweis University, Üllői út. 26, H-1085

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• Yordanka Mollova-Sapundzhieva Plamen Angelov Danail Georgiev Pavel Yanev Department of Organic Chemistry, University of Plovdiv Paisii Hilendarski, 24 Tsar Asen Str., 4000 Plovdiv, Bulgaria Department of Biochemistry and Microbiology, University of Plovdiv Paisii Hilendarski, 24 Tsar Asen Str

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• Tinglan Liu Yu Zhou Junhong Tang Chengming Wang Department of Chemistry, Jinan University, Guangzhou 511443, P. R. China UNITEST, Weifang 261000, P. R. China 10.3762/bjoc.19.131 Abstract Photoredox catalysis plays a crucial role in contemporary synthetic organic chemistry. Since the

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

• ; Department of Organic Chemistry, Biochemistry and Catalysis, Research Centre of Applied Organic Chemistry, 90-92 Panduri Street, RO-050663 Bucharest, Romania 10.3762/bjoc.19.130 Abstract Mechanically interlocked molecules (MIMs) have been important synthetic targets in supramolecular chemistry due to their

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• Lisa-Lou Gracia Philip Henkel Olaf Fuhr Claudia Bizzarri Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Kaiserstrasse 12, 76131 Karlsruhe, Germany Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Kaiserstrasse 12, 76131 Karlsruhe, Germany

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• Anastasia A. Fesenko Anatoly D. Shutalev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation 10.3762/bjoc.19.126 Abstract The transformation of 3-[(ethoxymethylene)amino]-1-methyl-1H-pyrazole-4-carbonitrile into the 14

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• materials. Radical depolymerization, an efficient approach to destroy polymers, finds applications in two distinct fields, semiconductor industry and environmental protection. Polymer chemistry has largely diverged from organic chemistry with the fine division of modern science but polymer chemists

• polymerization; Introduction Early last century, with the groundbreaking macromolecular hypothesis by Hermann Staudinger [1], polymer science was born out of organic chemistry. Since then, polymer science has evolved into an important branch of physical science and a fundament of the modern life. Like many

• inextricably linked to organic chemistry. However, the two fields took divergent paths over the past century. Many emergent radical chemistries in the organic chemistry community has not yet found a place in the polymer science. We believe this gap will narrow with a broader use of chemical informatics tools

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

• techniques. Some energy-economic reactors such as ball mill, microwave, ultrasound and, most importantly, flow reactors have also evolved towards a more sustainable future. To showcase the modern approaches in this domain, this thematic issue in the Beilstein Journal of Organic Chemistry gathers recent

Unraveling the role of prenyl side-chain interactions in stabilizing the secondary carbocation in the biosynthesis of variexenol B

• Moe Nakano,
• Rintaro Gemma and
• Hajime Sato

Beilstein J. Org. Chem. 2023, 19, 1503–1510, doi:10.3762/bjoc.19.107

• offer many valuable insights from a fundamental organic chemistry perspective. The terpene cyclization cascade generally involves a multistep domino-type reaction. Therefore, it is challenging to reveal the detailed reaction mechanism solely by an experimental method. To address this issue

Cyclization of 1-aryl-4,4,4-trichlorobut-2-en-1-ones into 3-trichloromethylindan-1-ones in triflic acid

• Vladislav A. Sokolov,
• Andrei A. Golushko,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2023, 19, 1460–1470, doi:10.3762/bjoc.19.105

• Vladislav A. Sokolov Andrei A. Golushko Irina A. Boyarskaya Aleksander V. Vasilyev Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia Department of Chemistry, Saint Petersburg State Forest

Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs

• Binbin Gu,
• Lin-Fu Liang and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1452–1459, doi:10.3762/bjoc.19.104

• Binbin Gu Lin-Fu Liang Jeroen S. Dickschat Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany 10.3762/bjoc.19.104 Abstract Two aspects of the biosynthesis of the non-canonical terpene synthase for 2-methylisoborneol have been

Functional characterisation of twelve terpene synthases from actinobacteria

• Anuj K. Chhalodia,
• Houchao Xu,
• Georges B. Tabekoueng,
• Binbin Gu,
• Kizerbo A. Taizoumbe,
• Lukas Lauterbach and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100

• Anuj K. Chhalodia Houchao Xu Georges B. Tabekoueng Binbin Gu Kizerbo A. Taizoumbe Lukas Lauterbach Jeroen S. Dickschat Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany 10.3762/bjoc.19.100 Abstract Fifteen type I terpene

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

• Feng Chen,
• Xiu-Hua Xu,
• Zeng-Hao Chen,
• Yue Chen and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

• Feng Chen Xiu-Hua Xu Zeng-Hao Chen Yue Chen Feng-Ling Qing Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China Shandong Dongyue Polymer Material Co., Ltd

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• interest in developing novel methodologies in this field of organic chemistry. Keywords: alkylation; cross-dehydrogenation coupling; ether; non-noble metals; Introduction Since the 1970s, organic chemists have developed many selective cross-coupling methods for the construction of C–C bonds, such as the

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates

• Olfa Mhasni,
• Jalloul Bouajila and
• Farhat Rezgui

Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93

• Toulouse, France University of Tunis El Manar, Laboratory of Organic Chemistry, Faculty of Sciences, Campus, 2092 Tunis, Tunisia 10.3762/bjoc.19.93 Abstract A highly α-regioselective N-nucleophilic allylic substitution of cyclic MBH alcohols and acetates with imidazole or benzimidazole, in toluene at

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• David T. Nemoto Jr Kang-Jie Bian Shih-Chieh Kao Julian G. West Department of Chemistry, Rice University, 6100 Main St MS 602, Houston, TX 77005, USA 10.3762/bjoc.19.90 Abstract The place of alkyl radicals in organic chemistry has changed markedly over the last several decades, evolving from

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• Valeriy O. Filimonov Alexandra I. Topchiy Vladimir G. Ilkin Tetyana V. Beryozkina Vasiliy A. Bakulev Technology of Organic Synthesis Department, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st. Yekaterinburg 620002, Russia Department of Organic Chemistry

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• Dmitry B. Vinogradov Alexei N. Izmest'ev Angelina N. Kravchenko Yuri A. Strelenko Galina A. Gazieva N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation 10.3762/bjoc.19.80 Abstract A series of imidazo[4,5-e][1,3]thiazino

• . Acknowledgements Crystal structure determination was performed in the Department of Structural Studies of the N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences.

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• the tremendous progress in organic chemistry over the last few decades, metal catalysis has been increasingly and successfully replaced by organocatalysis, i.e., accelerating the rate of chemical transformations by using small organic molecules as catalysts. Although being discovered more than 100