Search results

Search for "C–H-functionalization" in Full Text gives 125 result(s) in Beilstein Journal of Organic Chemistry.

Recent advances in electrochemical copper catalysis for modern organic synthesis

  • Yemin Kim and
  • Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

Graphical Abstract
  • catalysis to organic synthesis, focusing on recent developments in Cu-catalyzed electrochemical reaction categorized into four types: 1) CH functionalization, 2) olefin addition, 3) decarboxylative functionalization, and 4) coupling reactions (Figure 3). This review aims to provide insight into the
  • potential of copper-based electrochemical methodologies while also inspiring future research in this rapidly growing field. Review CH Functionalization Site- and chemoselective CH functionalization has emerged as a powerful platform for the formation of new C–C and C–heteroatom bonds, offering an
  • Cu-catalyzed electrochemical C–H activation strategy through C–H alkynylation of arylamides followed by electrooxidative cascade annulation (Figure 4) [48]. This reaction enables sustainable CH functionalization by utilizing electricity as the terminal oxidant instead of stoichiometric amounts of
PDF
Album
Review
Published 16 Jan 2025

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

Graphical Abstract
  • multicomponent synthesis of acyclic and heteropolycyclic systems under copper(II) triflate catalysis are reported. Using alkenes and alkynes as substrates, various types of reactions were considered, including hydroamination, condensation, cross-coupling, CH functionalization, cycloaddition, aza-Diels–Alder
PDF
Album
Review
Published 14 Jan 2025

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

Graphical Abstract
  • . Keywords: CH functionalization; oxidation; peroxidation; radical reactions; TBHP; Introduction Organic peroxides are used in many different areas of human activities. The traditional and most developed field is the use of peroxides as initiators in the polymerization process for the production of a wide
PDF
Album
Review
Published 18 Nov 2024

C–H Trifluoromethylthiolation of aldehyde hydrazones

  • Victor Levet,
  • Balu Ramesh,
  • Congyang Wang and
  • Tatiana Besset

Beilstein J. Org. Chem. 2024, 20, 2883–2890, doi:10.3762/bjoc.20.242

Graphical Abstract
  • various transformations [54][55][56][57][58][59][60][61][62][63][64]. In consequence, a large number of transition-metal-catalyzed or radical-mediated processes for CH functionalization of aldehyde hydrazones has flourished over the years. An ideal scenario for a direct and sustainable synthetic route
  • towards trifluoromethylthiolated hydrazones will be the direct CH functionalization of the corresponding aldehyde hydrazone, an uncharted transformation to date. Forging a C–S bond by the direct C–H-bond functionalization of hydrazones is still underdeveloped. Except for transformations leading to the
PDF
Album
Supp Info
Full Research Paper
Published 12 Nov 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • industrial settings. An anodic oxidation is frequently employed for CH functionalization, which can simplify late-stage functionalization strategies. Additionally, many of these synthetic methods do not require precious metals, enhancing their appeal in terms of sustainability and cost-effectiveness
  • diselenides (Scheme 23b) [32]. 1.2 Organo-mediators-enabled anodic oxidation The Baran group has made significant contributions to the field of organic electrochemistry. One of their developments is the electrochemical allylic oxidation, a highly useful CH functionalization method applicable to several
  • efficient method for CH functionalization. The continuous flow setup allows for precise control over reaction conditions, enhanced mass transfer, and improved reaction kinetics, leading to higher efficiency and faster reaction times. In 2023, the Chiang group reported the photoelectrochemical homo-coupling
PDF
Album
Review
Published 09 Oct 2024

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

  • Phong Thai,
  • Lauv Patel,
  • Diyasha Manna and
  • David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

Graphical Abstract
  • ), Koser’s reagent (PhI(OH)OTs), Zhdankin’s reagent (C6H4(o-COO)IN3, ABX), and Dess–Martin periodinane (DMP) – and find application in an array of synthetically important transformations including olefin difunctionalization, carbonyl desaturation, alcohol oxidation, and CH functionalization [3][4
PDF
Album
Supp Info
Full Research Paper
Published 11 Sep 2024

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

  • Kevin Schofield,
  • Shayna Maddern,
  • Yueteng Zhang,
  • Grace E. Mastin,
  • Rachel Knight,
  • Wei Wang,
  • James Galligan and
  • Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

Graphical Abstract
  • flexibility [8]. Indeed, early incorporation of deuterium during hit generation may negate the need for late-stage CH functionalization which often requires strong external oxidants or affords products with significantly lower biological activity [25][26][27]. Thus, eight MCRs were evaluated for D-reagent
PDF
Album
Supp Info
Full Research Paper
Published 06 Sep 2024

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

  • Andrey R. Galeev,
  • Maksim V. Dmitriev,
  • Alexander S. Novikov and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

Graphical Abstract
  • mainly via metal-catalyzed C–N or C–C bond formation. Despite recent advances in the area of remote CH functionalization, this strategy still requires some pre-functionalization of the starting material or the use of directing groups [28][29][30][31][32]. An alternative strategy is based on aromatic
PDF
Album
Supp Info
Full Research Paper
Published 02 Sep 2024

From perfluoroalkyl aryl sulfoxides to ortho thioethers

  • Yang Li,
  • Guillaume Dagousset,
  • Emmanuel Magnier and
  • Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

Graphical Abstract
  • study, many research groups described a strategy for ortho-CH functionalization of aryl sulfoxides with various nucleophiles via a cascade reaction of interrupted Pummerer reaction/sigmatropic rearrangement (Scheme 1a) [6][7][8][9][10][11]. A large range of nucleophiles, such as phenols [12][13][14][15
PDF
Album
Supp Info
Full Research Paper
Published 23 Aug 2024

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

  • Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

Graphical Abstract
  • access to diazo compounds as either synthetic intermediates or products. A special attention is paid to the reaction mechanism with the aim to encourage further development in this field. Keywords: CH functionalization; diazo compound; electrosynthesis; hydrazone; nitrogen-containing heterocycle
PDF
Album
Review
Published 14 Aug 2024

Benzylic C(sp3)–H fluorination

  • Alexander P. Atkins,
  • Alice C. Dean and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

Graphical Abstract
  • . This review aims to give context to these transformations and strategies, highlighting the different tactics to achieve fluorination of benzylic C–H bonds. Keywords: benzylic; CH functionalization; fluorination; photoredox catalysis; Introduction The development of new fluorination methodologies is
PDF
Album
Review
Published 10 Jul 2024

Predicting bond dissociation energies of cyclic hypervalent halogen reagents using DFT calculations and graph attention network model

  • Yingbo Shao,
  • Zhiyuan Ren,
  • Zhihui Han,
  • Li Chen,
  • Yao Li and
  • Xiao-Song Xue

Beilstein J. Org. Chem. 2024, 20, 1444–1452, doi:10.3762/bjoc.20.127

Graphical Abstract
  • hypervalent iodine(III) reagents has been developed [12][13][14][15][16][17] (Figure 1), including the well-known Zhdankin reagents [13] and Togni reagents [14]. These reagents are popularly used as electrophilic group transfer reagents [18][19] in a variety of reactions, such as CH functionalization [20][21
PDF
Album
Supp Info
Letter
Published 28 Jun 2024

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

  • Mithu Roy,
  • Bitan Sardar,
  • Itu Mallick and
  • Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

Graphical Abstract
  • –halogen bond formation, as well as CH functionalization [27]. Some notable examples include C–H arylation, various cross-coupling reactions, oxidative coupling, and photocatalytic radical reactions. The advantages of visible-light-induced photoredox catalysis are due to the ability to utilize visible
PDF
Album
Review
Published 14 Jun 2024

Nucleophilic functionalization of thianthrenium salts under basic conditions

  • Xinting Fan,
  • Duo Zhang,
  • Xiangchuan Xiu,
  • Bin Xu,
  • Yu Yuan,
  • Feng Chen and
  • Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

Graphical Abstract
  • -stage CH functionalization of arenes, Wickens’s group has introduced an oxidative alkene aziridination strategy that relies on thianthrenation of an alkene under electrochemical conditions [27]. Subsequently, cyclopropanation, [28] aziridination, [29] allylic CH functionalization, [30][31] transition
PDF
Album
Supp Info
Full Research Paper
Published 08 Feb 2024

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

Graphical Abstract
  •  15) [27]. This method involved a series of steps, including the formation of an EDA complex, decarboxylation, radical addition, CH functionalization, and annulation. Various primary, secondary, and tertiary alkyl N-hydroxyphthalimide esters 33 showed potential as viable substrates for the synthesis
PDF
Album
Review
Published 22 Nov 2023

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • of aryl sulfides by using the catalyst and the base. A catalytic cycle is shown in Scheme 4. Firstly, electrophilic Pd(TFA)2 generated from Pd(OAc)2 and TFA, which (by CH functionalization of arene 4) led to intermediate II. Oxidative insertion of intermediate II into the N–S bond of 1 afforded
PDF
Album
Review
Published 27 Sep 2023

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

Graphical Abstract
  • and the use of a ketone was necessary to induce CH functionalization selectivity in preference to C=C functionalization. The products were obtained in moderate to high yields (Scheme 67). 2.6 N–H and C(sp2)–H carboxylation The application of the [(IPr)CuOH] complex as catalyst for the N–H/C(sp2)–H
PDF
Album
Review
Published 20 Sep 2023

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

Graphical Abstract
  • significantly different reactivity and chemical selectivity from noble metals (Ru, Rh, Pd). Compared with noble metals, copper catalysts are cheaper and easier to obtain, making Cu more advantageous for industrial applications of CH functionalization reactions. The Glaser–Hay reaction may be one of the oldest
  • Cu-catalyzed oxidative coupling reactions [43]. However, due to complex mechanisms, Cu-catalyzed CH functionalization reactions developed only slowly in the last decade. Since recently the Cu-catalyzed oxidative coupling has emerged as a powerful synthetic strategy due to the development of CDC
  • ]. The current synthesis method depends on the reaction of organic borane with epoxy carbonyl compounds. Using the CDC reaction can save some synthesis steps [105]. Based on DDQ-mediated oxidative CH functionalization of benzyl ethers, the mechanism can be described as a single electron transfer (SET
PDF
Album
Review
Published 06 Sep 2023

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

Graphical Abstract
  • behavior of P450 oxygenases encouraged early work on site-selective CH functionalization [20]. Throughout their studies, it was found that manganese could perform the same HAT and RLT steps as iron at heme active sites. Groves developed the manganese tetramesitylporphine catalyst V (Scheme 2), which was
PDF
Album
Perspective
Published 15 Aug 2023

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

Graphical Abstract
  • of several methods for the synthesis of functionalized pyridines or their integration into an organic molecule, new methodologies for the direct functionalization of pyridine scaffolds have been developed during the past two decades. In addition, transition-metal-catalyzed CH functionalization and
  • the mechanisms involved. Keywords: CH functionalization; heterocycles; pyridine; rare earth metal; transition-metal-catalyzed; Introduction Pyridine, one of the most important azaheterocyclic scaffolds, is found in a diverse range of bioactive natural products, pharmaceuticals, and functional
  • functionalize a C–H bond in pyridine with traditional chemical transformations. On the other hand, intriguing developments have been made for the functionalization of inert C–H bonds in organic synthesis during the past two decades. In this regard, the transition-metal-catalyzed CH functionalization has made
PDF
Album
Review
Published 12 Jun 2023

Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles

  • Deepak Singh,
  • Shyamal Pramanik and
  • Soumitra Maity

Beilstein J. Org. Chem. 2023, 19, 666–673, doi:10.3762/bjoc.19.48

Graphical Abstract
  • from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay CH functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic
  • products with excellent yields and regioselectivity, thus confirming excellent functional group tolerability. Keywords: CH functionalization; imidazo heterocycles; photoredox; regioselective; relay catalysis; Introduction Among all N-fused heterocycles, imidazo[1,2-a]pyridines (IPs) are the prevalent
  • aerobic oxygenation approach to imidazo heterocycles II to install the hydroxymalonate unit onto I through sequential photoredox CH functionalization. Till date, there is no report of the direct incorporation of a quaternary hydroxyalkyl, specifically a hydroxymalonyl group at the C-3 position of IPs
PDF
Album
Supp Info
Letter
Published 12 May 2023

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

  • Grédy Kiala Kinkutu,
  • Catherine Louis,
  • Myriam Roy,
  • Juliette Blanchard and
  • Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

Graphical Abstract
  • system was thus found to be compatible with the realization of this type of CH functionalization. This process led to a significant reduction of the reaction time compared to the batch, in particular by increasing the temperature to 200–250 °C, without significant losses of activity and selectivity
PDF
Album
Supp Info
Full Research Paper
Published 03 May 2023

Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

  • Martina Mamone,
  • Giuseppe Gentile,
  • Jacopo Dosso,
  • Maurizio Prato and
  • Giacomo Filippini

Beilstein J. Org. Chem. 2023, 19, 575–581, doi:10.3762/bjoc.19.42

Graphical Abstract
  • tool to guide the development of greener and more convenient synthetic protocols [7][8][9][10][11][12]. In this context, photochemical approaches based on electron donor–acceptor (EDA) complexes have been successfully exploited to drive the direct CH functionalization of a large number of organic
PDF
Album
Supp Info
Letter
Published 27 Apr 2023

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

Graphical Abstract
  • reaction to afford the naphthalene product 88a. Inspired by Zhao’s seminal report on the racemic carboamination of bicyclic alkenes [53], the Cramer laboratory studied the Co-catalyzed enantioselective carboamination of bicyclic alkenes 1 via CH functionalization in 2021 (Scheme 17) [54]. The authors
  • [2.3.1]-bicyclic alkenes 158 for the synthesis of isoquinoline (160) or isoquinolone-fused bicycles 162 (Scheme 28) [74]. Compared to their previous CH functionalization reaction (Scheme 27) [73], no ring opening was observed. This reaction with O-acetyl ketoximes was amenable to a variety of para
PDF
Album
Review
Published 24 Apr 2023

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

Graphical Abstract
  • ][57]. Stereoselective 5,6-dihydro-1,4-dithiin-based synthesis of cis-olefins [42][58]. Addition to aldehydes and applications in stereoselective synthesis. Direct CH functionalization methods for 1,4-dithianes [82][83]. Known cycloaddition reactivity modes of allyl cations [84][85][86][87][88][89][90
PDF
Album
Review
Published 02 Feb 2023
Other Beilstein-Institut Open Science Activities