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Search for "reductive elimination" in Full Text gives 171 result(s) in Beilstein Journal of Organic Chemistry.

Copper catalysis: a constantly evolving field

  • Elena Fernández and
  • Jaesook Yun

Beilstein J. Org. Chem. 2025, 21, 1477–1479, doi:10.3762/bjoc.21.109

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  • . In their contribution, Son et al. focus on transformations via the formation of copper nitrenoids, particularly amidations via oxidative insertion to N–O bonds and reductive elimination, and a small number of other reactions. The final Review by Cho, Lee, and co-workers is useful for the scientific
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Published 17 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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  • addition of the aryl halide, the disubstituted oxetane product is generated by a reductive elimination. Finally, the two catalytic cycles are closed by an oxidation/reduction process: the Fe(II) species is reoxidised by atmospheric oxygen and the Ni(I) complex is reduced by the added manganese powder. In
  • reduction of the Ni(II) pre-catalyst) via oxidative addition, radical coupling and reductive elimination. The last step is a single-electron transfer between the resulting Ir(II) and Ni(I) complexes, regenerating the active catalysts and closing the two cycles. In 2021, Romanov-Michailidis and Knowles et al
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Published 27 Jun 2025

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

Graphical Abstract
  • to generate σ-alkylpalladium(II) intermediate II, which is trapped by the α-carbonylalkyl radical A in the presence of Ag0 species [18]. Finally, reductive elimination occurs to yield the desired product. Inspired by the above work, a novel, general silver-catalyzed oxidative alkyletherification of
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Published 24 Jun 2025

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

  • Julius Seumer,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

Graphical Abstract
  • and carboxylic acid. The palladacycle intermediate can undergo further (coupling) reactions and form a variety of products via reductive elimination. In previous studies, the rate- and regioselectivity-controlling step was identified as the formation of the palladacycle [5][6][7]. The regioselectivity
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Published 16 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

Graphical Abstract
  • intermediate 85 followed by reductive elimination with tertiary amine to give intermediate 86. The utilization of earth-abundant transition metals for O/N-acylation has emerged due to their low cost. For instance, Son and co-workers (2023) utilized a more cost-efficient Cu salt to access N-acyliminophosphorane
  • 89 from the corresponding dioxazolone 88 in excellent yields via reductive elimination from intermediate 90 (Scheme 26) [62]. Hu and co-workers (2019) also employed a Cu salt (Cu(OTf)2) to synthesize N-difluoroethylimide 91 from cinnamic acid (7) and tert-butyl nitrite (TBN) in good yield via
  • (Scheme 63B) [110]. On the other hand, Yao and co-workers (2023) used alkenyl halides 240 and formate salts to prepare cinnamic ester 24 catalyzed by a Ru complex via an oxidative addition/reductive elimination cycle involving intermediates 241–243 (Scheme 64) [111]. The method has been successfully
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Published 28 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

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  • , tetrabutylammonium iodide (TBAI), and water significantly accelerated aryne generation, thereby increasing its local concentration. This favored aryne coordination to the palladium center, followed by CO insertion and reductive elimination to furnish phenanthridinones. In contrast, when dppm was introduced
  • preferentially occupied the palladium coordination site. Sequential insertion of CO and aryne, followed by reductive elimination, culminated in acridone formation. This ligand-dependent mechanistic dichotomy underscores the critical interplay between aryne availability, steric modulation, and electronic effects
  • the hydroxy group to form complex Int-17 and the amino group undergoes nucleophilic attack to generate Int-18. After CO insertion complex Int-19 is produced and reductive elimination ultimately affords the indolo[3,2-c]coumarin product 10. In 2023, the Garg group achieved the first example of
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Published 07 May 2025

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

  • Xuhong Zhao,
  • Weishuang Li,
  • Mengli Yang,
  • Bojie Li,
  • Yaoyao Zhang,
  • Lizhen Huang and
  • Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

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  • , which acts as a base. Subsequently, I undergoes oxidative addition and complexation with the amidine 2 to generate intermediate II. This intermediate then undergoes reductive elimination to form intermediate III, releasing CS@CuI back into the system. Finally, the coupling reaction between the carboxyl
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Published 28 Apr 2025

Recent advances in the electrochemical synthesis of organophosphorus compounds

  • Babak Kaboudin,
  • Milad Behroozi,
  • Sepideh Sadighi and
  • Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

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  • reaction proceeded via an oxidative addition and reductive elimination processed in the presence of Ni(0), which was produced in situ from NiBr2 in the cathode. Palladium is one of the most important metals used as a catalyst in non-electrochemical reactions. In 2020, Budnikova et al. [58] reported a
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Published 16 Apr 2025

Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

  • Xiao-Yang Bi,
  • Xiao-Shuai Yang,
  • Shan-Shan Chen,
  • Jia-Jun Sui,
  • Zhao-Nan Cai,
  • Yong-Ming Chuan and
  • Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47

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  • acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known
  • steps and achieved 12% overall yield. In May 2024, the Qin group reported the second total synthesis of (±)-simonsol C (Scheme 2) [5]. An effective strategy to form the 6/5/6 benzofuran scaffold was developed which specifically involved a basic dearomatization and reductive elimination with Zn/AcOH to
  • dearomatization offers considerable versatility. Not only can it be employed under basic dearomatization conditions, but it is also effective under Lewis acid conditions. Combined with a reductive elimination using Zn/AcOH, the benzofuran skeleton can be easily synthesized. This dual applicability of the new
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Published 17 Mar 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • the same amine component) deprotonates the terminal alkyne, generating the metal acetylide derivative A, which is the active nucleophilic species in the reaction. Intermediate A undergoes an oxidative addition by the dihaloalkane, generating intermediate B. This undergoes reductive elimination to
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Published 13 Mar 2025

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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  • reaction mixture. This step allows the oxidative addition of nickel on the aryl bromide 9 followed by the reductive elimination giving the desired product 11. Besides the innovative synthetic results obtained in this study, the authors underline a major advantage to switch to red light as it enables a
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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

Graphical Abstract
  • , providing the corresponding products (16g–k). Mechanistically, the reaction begins with the generation of the active copper species 17, successively forming INT-19 and INT-20 (Figure 5). The penta-coordinated copper nitrenoid species INT-20, as suggested by DFT calculations, undergoes reductive elimination
  • 20 is afforded through protonolysis, regenerating the active copper species to complete the catalytic cycle. 2 Amidation via oxidative insertion to N–O bonds and reductive elimination 2.1 Hydroamidation of vinylarenes Amines bearing stereogenic centers have been widely investigated in the research
  • and silane, undergoes the enantio-determining hydrocupration of the vinylarene, affording INT-25 [25]. Next, oxidative insertion of INT-25 into the N–O bond of the dioxazolone, forms INT-26, followed by decarboxylative reductive elimination to generate INT-27. Further incorporation of silane delivers
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Published 22 Jan 2025

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
  • through oxidative addition, followed by transmetalation and reductive elimination, to obtain the desired product. Throughout the catalytic cycle, the catalyst undergoes conversion between [M]n and [M]n+2 (Figure 1) [11]. However, using alkyl electrophiles as coupling partners in cross-coupling reactions
  • elimination, produces C–H alkynylated arene 10, which then forms the final product 3 through intramolecular cyclization. Finally, the Cu(I) complex 9 produced via reductive elimination is reoxidized at the anode to regenerate the Cu(II) complex 4, completing the catalytic cycle. Yao and Shi developed the
  • pair (AQDS•−, 20•+) then generate a benzylic radical 23 and a semiquinone radical ([AQDS–H]•) through proton transfer. The benzylic radical intermediate 23 subsequently reacts with the chiral copper catalyst L3Cu(II)(CN)2 (25) to form a Cu(III) complex 26, which undergoes reductive elimination to
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Published 16 Jan 2025

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

  • Takeshi Fujita,
  • Haruna Yabuki,
  • Ryutaro Morioka,
  • Kohei Fuchibe and
  • Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

Graphical Abstract
  • , reductive elimination from G yields the coupling products 3. The following experiments were performed to elucidate the mechanism. Under the same conditions as the coupling reaction, stoichiometric amounts of Ni(cod)2, PCy3, and cod were treated with fluoronaphthofuran 1b at room temperature for 13 h
  • simultaneously between E and the arylboronic acids 2, leading to the formation of G (Scheme 5, path c). The intermediates G then undergo reductive elimination to yield 3. To assess the impact of halogen substituents, we also examined reactions of 2-halogenated benzofurans 1a-X (1a-Cl: X = Cl; 1a-Br: X = Br; 1a-I
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Published 15 Jan 2025

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

  • Radell Echemendía,
  • Carlee A. Montgomery,
  • Fabio Cuzzucoli,
  • Antonio C. B. Burtoloso and
  • Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

Graphical Abstract
  • reductive elimination (path 1) [37][38][39]. This pathway initiates by formation of a halogen bond complex between 1a and the trifuoroethyl(mesityl)iodonium ion 2a’, where adduct XB-1 is presumably in equilibrium with isomeric XB-2. Reductive elimination of the iodoarene from XB-2 would furnish B, whose
  • arene moieties. These observations confirmed the LUMO as an appropriate lobe for nucleophilic attack via the SN2 pathway (path 2), and confirmed the LUMO+1 as an appropriate lobe for substitution via reductive elimination (path 1). As such, neither mechanism could be immediately discarded, and we were
  • mesh) as a stationary phase (eluent n-hex/AcOEt 5:95%). Representative examples of fluorine containing, biologically active compounds. Possible mechanisms for the reaction of 1a and 2a leading to 3a (via B), proceeding via either halogen-bonded adducts and reductive elimination (path 1) or directly via
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Published 04 Dec 2024

Hypervalent iodine-mediated intramolecular alkene halocyclisation

  • Charu Bansal,
  • Oliver Ruggles,
  • Albert C. Rowett and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

Graphical Abstract
  • ring A (Scheme 2). The Pd(II) intermediate is oxidised by PhI(OPiv)2/AgF, forming Pd(IV). Formation of the product can occur either by reductive elimination by Pd(IV) or SN2 nucleophilic attack by fluorine with concomitant palladium reduction. Reductive elimination of the Pd(II) intermediate forms the
  • , including ligand coupling, oxidative addition, intermolecular nucleophilic attack, 1,2-aryl migration, reductive elimination, and intramolecular nucleophilic attack. This approach offers a rapid and effective way to produce 5-fluoro-2-aryloxazoline compounds, which are valuable building blocks in organic
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Published 28 Nov 2024

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

  • Cesia M. Aguilar-Morales,
  • América A. Frías-López,
  • Nadia V. Emilio-Velázquez,
  • Alejandro Islas-Jácome,
  • Angelica Judith Granados-López,
  • Jorge Gustavo Araujo-Huitrado,
  • Yamilé López-Hernández,
  • Hiram Hernández-López,
  • Luis Chacón-García,
  • Jesús Adrián López and
  • Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

Graphical Abstract
  • first catalytic cycle begins with the coupling of 1,5-disubstituted tetrazole-alkyne 19 and methanesulfonyl-2-iodoaniline 17 forming the intermediate 23. Following a reductive elimination, the Sonogashira-like product 24 is produced, which then progresses into the second catalytic cycle. In this cycle
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Published 26 Nov 2024

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

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  • the benzyl carbocation F, which is intercepted by TBHP. In pathway 2 the formation of 181 occurs through a two-step outer-sphere ligand transfer between Cu(II)OO-t-Bu and the benzyl radical E. Pathway 3 proposes the formation of Cu(III) complex H, followed by reductive elimination and the formation of
  • aid of the ortho-directing group to give the palladium intermediate B, which undergoes reductive elimination to establish the C−C bond. A Cu-catalyzed difunctionalization of styrenes 211 with TBHP and N-hydroxyphthalimide (NHPI) (212) as sources of O-functional groups was reported (Scheme 66) [135
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Published 18 Nov 2024

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

  • Ritu Mamgain,
  • Kokila Sakthivel and
  • Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

Graphical Abstract
  • reductive elimination in exceptional yields (Scheme 20) [71]. Although screening studies indicated the possibility of achieving the N-arylation at both, the N1- and N2-positions of the triazoles, N2-arylation was predominantly observed. It was incredible to achieve splendid regioselectivity without the
  • the study. The results demonstrated that the diphenyliodonium triflate has a feasible energy barrier of 21.5 kcal/mol and can be readily converted into a stable iodonium thiolate species. This species can further undergo a C–S bond-forming reductive elimination, providing the sulfide product. As a
  • , reductive elimination of intermediate C yields the desired sulfoxides 87 (Scheme 36). Recently, a detailed study by Thakur and group on the metal-free arylation of tetrazole-5-thiols 88, exploring various substrate scopes under optimized conditions was conducted (Scheme 37) [90]. The findings indicated a
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Published 13 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
  • carboxylate substrate and [Ru(p-cymene)Cl2]2. Subsequently, the Ru complex coordinates with the aniline substrate, followed by C–H activation to form a six-membered Ru species. The final product is generated through reductive elimination, releasing Ru(0), which is then reoxidized on the anode to regenerate
  • mechanism. Initially, C–H activation occurs, resulting in the formation of a cyclometalated Ir(III) intermediate. Ligand exchange with the alkyne substrate, followed by migratory insertion, leads to the formation of a seven-membered 18-electron Ir(III) complex. This complex then undergoes reductive
  • elimination (RE) to produce an 18-electron Ir(I) complex. The Ir(I) complex is subsequently anodically oxidized back to an Ir(III) complex, with the concomitant elimination of the product. This protocol can be applied to the LSF and diversification of natural products, as demonstrated by the examples of
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Published 09 Oct 2024

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

  • Yutaro Miyashita,
  • Sae Someya,
  • Tomoko Kawasaki-Takasuka,
  • Tomohiro Agou and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

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  • of the reductive elimination very slow, the intermediary Cu(III) species safely existed until the addition of D2O. Because the significant overlap of NMR peaks was observed due to the quite similar structure of 11a and 11a-D, quantitative analysis of the deuterium content of 11a-D was not possible
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Published 25 Sep 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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Published 16 Aug 2024

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

  • Ze-Nan Hu,
  • Yan-Hui Wang,
  • Jia-Bing Wu,
  • Ze Chen,
  • Dou Hong and
  • Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

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  • then undergoes a proton shift to provide intermediate B. Intermediate B collapses via reductive elimination to give nitrenium ion C, along with the release of iodobenzene and sulfamate. Finally, nucleophilic attack of the olefin moiety of C on the electrophilic nitrogen atom, followed by the
  • migration and reductive elimination, along with the release of iodobenzene and sulfamic acid. Cyclization of protonated G takes place to afford the intermediate H. Finally, release of water and β-proton elimination produces the rearranged product 3a (Scheme 8). Conclusion In summary, we reported the
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Published 07 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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  • then reacted with a different isocyanide (R4–NC) in the presence of a palladium catalyst. The release of nitrogen from intermediates I resulted in nitrenes II, which in turn involved in the intramolecular transfer to yield species III. The carbodiimides IV, which were formed through reductive
  • elimination of III, underwent intramolecular cyclization to deliver the desired products 85. The scope of reaction showed that higher yield (57–90%) of 85 were obtained when benzaldehydes 83 were equipped with electron-donating groups (R1) and when bulky groups, such as 1-adamantyl or t-Bu (R4), were
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Published 01 Aug 2024

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

  • Samuel M. G. Dearman,
  • Xiang Li,
  • Yang Li,
  • Kuldip Singh and
  • Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

Graphical Abstract
  • ] reacted a perfluorinated iodine(III) compound with XeF2 and postulated the formation of a (perfluoroalkyl)iodine(V) difluoride intermediate which underwent a reductive elimination to afford perfluorinated products (Scheme 2C). In 2019 Togni reported a safer route to a range of acyclic iodine(V) fluorides
  • to a trans-configuration because of the bicyclic carbon skeleton. Trifluoroiodane 3, on the other hand, has both trans- and cis-configurations of the fluorine ligands which could play a key role in the reductive elimination step in the fluorination of phenylmagnesium bromide. Trifluoroiodane 3 also
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Published 29 Jul 2024
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