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Search for "phenanthroline" in Full Text gives 108 result(s) in Beilstein Journal of Organic Chemistry.

Red light excitation: illuminating photocatalysis in a new spectrum

  • Lucas Fortier,
  • Corentin Lefebvre and
  • Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

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  • band. These combined effects can be illustrated in the case of the [M(phen)3]2+ set with iron, ruthenium, and osmium (Figure 1). For a same phenanthroline ligand, these three complexes show an MLCT absorption band at different wavelengths, i.e., 522 nm for [Fe(phen)3]2+ [14], 449 nm for [Ru(phen)3]2
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Published 07 Feb 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

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  • conducted using a catalytic amount of copper acetate and a phenanthroline ligand, with a stoichiometric amount of silane serving as the reductant. Both aryl- and alkyl-substituted dioxazolones proved to be compatible under the standard reaction conditions, yielding the desired primary amides 28a–f. Notably
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Published 22 Jan 2025

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

  • Yongming Xiong,
  • Xue Lin Ma,
  • Shilong Su and
  • Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

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  • yield of 90%. Then, the Ni-mediated Yamamoto coupling reaction of 6 enabled cyclotrimerization to give trione 1 in a yield of 30%. It is worth mentioning that using 1,10-phenanthroline as the ligand in the Yamamoto coupling [25][26] led to a higher yield of compound 1 than using 2,2’-bipyridine. With
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Published 02 Jan 2025

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

  • Yuki Nakanishi,
  • Shoichi Sugita,
  • Kentaro Okano and
  • Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

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  • fused structure toward a phenanthroline diamide (Phen-2,9-diamide) [23] can be achieved by employing a palladium-catalyzed intramolecular C–H arylation [24][25][26][27][28]. One of the thus obtained products exhibited a remarkable extraction performance for a lanthanide ion, in which a metal-specific
  • of the palladium-catalyzed C–H arylation of phenanthroline to other nitrogen-containing heteroaromatic compounds. It is therefore intriguing to demonstrate the advantage of the palladium-catalyzed intramolecular C–H arylation compared to other protocols for the construction of related ring structures
  • conditions. We carried out the palladium-catalyzed intramolecular coupling reaction of precursor 1a under similar conditions [23], which afforded smooth reaction with phenanthroline bisamide, with 10 mol % of palladium acetate as a catalyst in the presence of potassium carbonate and tetra-n-butylammonium
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Published 13 Dec 2024

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

  • Marzieh Norouzi,
  • Mohammad Taghi Nazeri,
  • Ahmad Shaabani and
  • Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

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  • with 1,10-phenanthroline as cyclic imine under solvent-free conditions for the synthesis of pyrrole-fused phenanthroline. This reaction proceeds via in situ formation of zwitterion I through reaction of the aldehyde and malononitrile followed by 1,3-dipolar cycloaddition (Scheme 1a) [41]. Chen and co
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Published 11 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

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Published 09 Oct 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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  • [135]. Following this, a one-pot process involving Michael addition/cyclocondensation with hydrazine derivatives leads to the corresponding pyrazoles. Since magnesium ions are formed during the Kumada coupling, the additive phenanthroline must be added during the cyclization step to prevent the
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Published 16 Aug 2024

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

  • Mohd Farhan Ansari,
  • Atul Kumar Maurya,
  • Abhishek Kumar and
  • Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

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  • alkylation of methylene ketones with primary alcohols using a phosphine-free and commercially available Mn(acac)2/1,10-phenanthroline system [60]. Various methylene ketones and alcohols were investigated with Mn(acac)2 (2.5 mol %) as a precursor, 1,10-phenanthroline (3 mol %) as ligand, and t-BuOK (1 equiv
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Published 21 May 2024

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

  • Tural N. Akhmedov,
  • Ajeet Kumar,
  • Daken J. Starkenburg,
  • Kyle J. Chesney,
  • Khalil A. Abboud,
  • Novruz G. Akhmedov,
  • Jiangeng Xue and
  • Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

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  • in Table S2 (Supporting Information File 1). First, the starting material 7e was obtained using 1,10-phenanthroline under harsh conditions as shown in Scheme 3 [29]. The same condensation reaction that worked for structurally similar 6a, produced a poorly separable mixture in the case of 7a. In the
  • secured due to the favorable hydrogen bonding (O–H∙∙∙N) between the oxime units; this idea is supported by 1H NMR spectroscopy which shows the presence of two distinct hydroxyl proton signals. The reduction of 7d in the presence of Pd/C and hydrazine monohydrate afforded 1,10-phenanthroline-5,6-diamine
  • ; HRESIMS: [M + H]+ calcd for C18H10N4O2, 315.0881; found, 315.0877. 10,13-Dihydropyrazino[2',3':5,6]pyrazino[2,3-f][1,10]phenanthroline-11,12-dione (7b) In a 100 mL three-neck round-bottom flask, compounds 12 (100 mg, 0.624 mmol) and 7e (150 mg, 0.713 mmol) were added to 15 mL of tetrahydrofuran (THF
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Published 08 May 2024

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

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  • conditions. In addition, Pd(phen)2(BF4)2 and Pd(tfa)2 in conjunction with tertramethyl-1,10-phenanthroline (tm-phen) reactivity were investigated. The process was generalized: by using Pd(OAc)2 (1–1.5 mol %) and 1,10-phen (2–3 mol %) to catalyze the reaction of some substrates and Pd(tfa)2 (0.1–1 mol %) and
  • of the Pd(dba)2/dppp/1,10-phen catalyst system. Synthesis of indoles from o-nitrostyrenes by using Pd(OAc)2 and Pd(tfa)2 in conjunction with bidentate nitrogen ligands: 1,10-phen (1,10-phenanthroline) and tm-phen (3,4,7,8-tetramethyl-1,10-phenanthroline). Synthesis of substituted 3-alkoxyindoles via
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Published 30 Apr 2024

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

  • Vladimir P. Rybalkin,
  • Sofiya Yu. Zmeeva,
  • Lidiya L. Popova,
  • Irina V. Dubonosova,
  • Olga Yu. Karlutova,
  • Oleg P. Demidov,
  • Alexander D. Dubonosov and
  • Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

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  • a terminal phenanthroline receptor substituent was synthesized. Upon irradiation in acetonitrile or DMSO with light of 436 nm, they underwent Z–E isomerization of the C=C bond, followed by very fast N→O migration of the acyl group and the formation of nonemissive O-acylated isomers. These isomers
  • sequential addition of Fe2+ and AcO−, we synthesized N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline substituent and studied the spectral-luminescent, photochromic and ionochromic properties. The phenanthroline moiety was incorporated into the molecule due to the
  • ]thiophene-3(2Н)-ones 2a–c with a terminal phenanthroline substituent was (E)-2-(((1,10-phenanthrolin-5-yl)amino)methylene)benzo[b]thiophen-3(2H)-one (1), obtained by condensation of 3-hydroxybenzo[b]thiophene-2-carbaldehyde with 5-aminophenanthroline in acetonitrile (Scheme 1). (Z)-N-((3-Oxobenzo[b]thiophen
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Published 11 Mar 2024
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  • -phenanthroline-based rotaxane 50 by employing the [2 + 2] CA–RE reaction, as shown in Scheme 17 [123]. The initial threading reaction involving the rod molecule 47 and macrocycle 48, constructed using [Cu(MeCN)4]PF6, resulted in the formation of the pseudorotaxane 49. The ensuing [2 + 2] CA–RE reaction of 49
  • room-temperature solution (dichloromethane) and as a frozen matrix at 77 K [123]. This is in contrast with the typical homoleptic phenanthroline-based CuI complexes renowned for their emissions from a triplet metal-to-ligand charge transfer excited state. The absence of luminescence may be attributed
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Published 22 Jan 2024

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

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  • interested in the development of earth-abundant systems. In particular, we chose the heteroleptic complex [Cu(dmp)DPEPhos](BF4), where dmp is 2,9-dimethyl-1,10-phenanthroline and DPEPhos is bis[(2-diphenylphosphino)phenyl] ether, which had been already successfully employed in other artificial photosynthesis
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Published 17 Nov 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

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  • -donors on the catalytic activity of NHC–Cu(I) complexes for azide–alkyne [3 + 2] cycloaddition reactions [67]. They determined binding constants of four NHC–CuCl complexes with two N-donors, which revealed that addition of phenanthroline to the NHC–CuCl enhanced the catalytic activity manifold. In fact
  • , on using [(SIMes)CuCl] with 1 mol % of phenanthroline for the [3 + 2] cycloaddition of benzyl azide with phenylacetylene, the yield of the product was 78% as against 10% in the absence of the N-donor (Scheme 49). Overall, two catalytic combinations 130a,b were found to give the best results. Cazin
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Published 20 Sep 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

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  • strong coordination of the pyridyl N-atom with Pd in the presence of a bidentate ligand was reported by Yu and co-workers [83]. They showcased the C3-selective olefination of pyridines using 1,10-phenanthroline, a bis-dentate ligand that weakens the coordination of the Pd catalyst with the pyridyl N-atom
  • groups used Pd(OAc)2 as catalyst with 1,10-phenanthroline as ligand. The group of Yu used aryl halides 137 as coupling partner, whereas the group of Tan utilized aryl tosylates 142 as coupling partner (Scheme 26). The Yu group also applied the developed protocol for the synthesis of the drug molecule
  • product 172 releasing a Rh(I) species. The Rh(III) species is regenerated in the presence of the copper salt. In another case of C3-(hetero)arylation, Yu and group [104] using palladium for C–H activation of pyridine with phenanthroline as a ligand developed a method in 2016 (Scheme 34). The authors
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Published 12 Jun 2023

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

  • Raphael Bereiter,
  • Marco Oberlechner and
  • Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

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  • 3,4-dihydropyran in dimethylformamide to obtain the corresponding tetrahydropyranyl-protected amine 17. Subsequently, a copper-catalyzed C–O bond formation at C6 using benzyl alcohol in the presence of caesium carbonate, copper(I) iodide, and 1,10-phenanthroline furnished benzyl ether 18 in excellent
  • -(tetrahydro-2H-pyran-2-yl)-1-deazapurine (18) Compound 17 (1.72 g, 5.23 mmol), copper(I) iodide (CuI, 99.52 mg, 0.52 mmol), 1,10-phenanthroline (188.35 mg, 1.05 mmol), caesium carbonate (Cs2CO3, 2.38 g, 7.32 mmol) and benzyl alcohol (BnOH, 1.13 g, 1.07 mL, 10.45 mmol) were suspended in 2.62 mL toluene (0.5 mL
  • )), 154.08 (H-C(2)), 162.52 (H-C(6)); ESIMS (m/z): [M + H]+ calcd for 151.06; found, 151.06. O6-Benzyl-1-deazahypoxanthine (31) Compound 17 (500 mg, 1.52 mmol), copper(I) iodide (CuI, 28.93 mg, 152 µmol), 1,10-phenanthroline (54.75 mg, 304 µmol), caesium carbonate (Cs2CO3, 692.93 mg, 2.13 mmol) and benzyl
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Published 29 Nov 2022

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

  • Yara Cristina Marchioro Barbosa,
  • Guilherme Caneppele Paveglio,
  • Claudio Martin Pereira de Pereira,
  • Sidnei Moura,
  • Cristiane Storck Schwalm,
  • Gleison Antonio Casagrande and
  • Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

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  • '-dimethylethanolamine (DMEA) and trans-1,2-diaminocyclohexane (DACH) were evaluated as ligands (Table 1, entries 18 and 19). However, the yield was lower compared to that obtained with 1,10-phenanthroline (phen). Control experiments were performed without catalyst (Table 1, entry 20), base (Table 1, entry 21), or
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Published 23 Aug 2022

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

  • Mio Matsumura,
  • Kaho Tsukada,
  • Kiwa Sugimoto,
  • Yuki Murata and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

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  • reaction between terminal alkynes and diimidazopyridinyl diselenides, generated from imidazo[1,2-a]pyridines and Se powder, using 10 mol % of CuI and 1,10-phenanthroline as the catalytic system under aerobic conditions. The C(sp2)–Se and C(sp)–Se bond-formation reaction can be performed in one-pot by using
  • ]. Guo, Han and Ma et al. also performed the synthesis of aryl imidazopyridinyl selenides in the presence of Ag2CO3 (2 equiv) and Cs2CO3 (2 equiv) using the CuI/1,10-phenanthroline catalytic system by replacing the aryl group donor with arylboronic acids [23]. Zhou et al. reported the reaction of Se
  • or dialkyl diselenides, followed by C–H selenation with imidazopyridines to form the corresponding compounds. We also reported the one-pot two-step reaction of Se powder with imidazopyridine and triarylbismuthines using the CuI/1,10-phenanthroline catalytic system without bases, which formed similar
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Published 19 Jul 2022

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

  • Prodip Howlader and
  • Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

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  • procedure developed by Sauvage on the basis of topological control [33] has found ample use in the preparation of rotaxane-based machines and devices [34]. A key element is a macrocyclic phenanthroline with an endotopic binding site as it precludes homoleptic complex formation. A further principle
  • PYridine and Phenanthroline complexes [85][86]), HETPHEN (HETeroleptic bisPHENanthroline complexes [87]) and HETTAP (HETeroleptic Terpyridine And Phenanthroline complexes [88]) interactions (Figure 12). Due to the different amount of donor atoms about the metal ion, the binding strength will decrease in
  • activity [94] (Figure 14). Because in any moment of the rotation there should at least one copper(I) phenanthroline be freed from contact with the monodentate rotator X, one would expect that the temporarily exposed copper(I) ions are catalytically active. It is important to note that this copper ion due
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Published 27 May 2022

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

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  • ]. The template complex (S)-3 was assembled by mixing the macrocycle (S)-1 (containing both a phenanthroline ligand and a BINOL unit) with [Cu(CH3CN4)]PF6 and the acyclic phenanthroline precursor 2. Then, the BINOL-based diiodide (S)-4 and Cs2CO3 were added successively over 18 hours. This resulted in
  • . Accordingly, demetalation leads to an almost complete disappearance of the CD signals in this area (see Figure 2). Saito and coworkers demonstrated that the homochiral [2]rotaxane (R)-10 can be efficiently synthesized using an active metal template approach [44][45]. The macrocyclic phenanthroline (R)-7 was
  • treated with copper iodide to obtain the phenanthroline–Cu(I) complex (R)-8. A Glaser-type coupling with the terminal alkynes 9, followed by demetalation, proceeds smoothly in 78% yield. This furnishes the desired chiral rotaxane (R)-10, consisting of a BINOL-based macrocycle and a diyne thread. The CD
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Published 06 May 2022

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

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  • steric effects. Anilkumar and co-workers reported an iron-catalyzed Sonogashira coupling of aryl iodides with terminal alkynes in the presence of a catalytic system made up of the greenest solvent, water, in the presence of 10 mol % FeCl3·6H2O and 20 mol % 1,10-phenanthroline as ligand under aerobic
  • , but their efficiencies were found to be lower than that of 1,10-phenanthroline. Metal impurities in FeCl3·6H2O were detected by using ICP mass spectrometry. Lipshutz and co-workers prepared nanoparticles from inexpensive iron(III) chloride containing reusable palladium in ppm level and XPhoS as ligand
  • synthesized 2-arylbenzo[b]furans by intramolecular arylation and Sonogashira cross-coupling of o-iodophenol with phenylacetylene/1-substituted-2-trimethylsilylacetylene under iron(III) catalysis in the presence of 5 mol % 1,10-phenanthroline as ligand and Cs2CO3 as base (Scheme 14) [31]. The use of 1,10
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Published 03 Mar 2022

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

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Published 07 Dec 2021

Visible-light-mediated copper photocatalysis for organic syntheses

  • Yajing Zhang,
  • Qian Wang,
  • Zongsheng Yan,
  • Donglai Ma and
  • Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

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  • cooperative steric hindrance based on bulky substituents at the 2,9-position of the phenanthroline moiety [32][33]. Alternatively, heteroleptic CuI complexes with phenanthroline and bulky chelating phosphine ligands were also synthesized [30][34][35]. The photophysical properties are dramatically modified by
  • studies included visible-light catalysis. In 2012, Reiser’s group [44] reported the allylation of α-haloketones 1 with olefins under irradiation (λ = 530 nm) in the presence of [Cu(dap)2Cl] (dap = 2,9-di(p-anisyl)-1,10-phenanthroline) as the catalyst. They conducted control experiments to establish that
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Published 12 Oct 2021

Photoredox catalysis in nickel-catalyzed C–H functionalization

  • Lusina Mantry,
  • Rajaram Maayuri,
  • Vikash Kumar and
  • Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

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  • transfer (HAT) and nickel catalysis [54]. The catalytic system consisting of iridium photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6, nickel catalyst NiBr2·3H2O, ligand 4,7-dimethoxy-1,10-phenanthroline (4,7-dOMe-phen), and 3-acetoxyquinuclidine was found to be optimal to afford the desired α-amino C–C coupled
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Published 31 Aug 2021

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

  • Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

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  • azidation was 7.5:1. Mn-catalyzed late-stage C–H azidation of bioactive molecules via electrophotocatalysis. a2.5 mol % of MnF2 was used. bNaN3 (5.0 equiv), MnF2 (10 mol %), 1,10-phenanthroline (20 mol %), TFA (4.0 equiv), and LiClO4 (2.0 equiv) were used with 4.5 mA for 15 h (5.0 mmol scale
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Published 26 Jul 2021
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