Hypervalent halogen chemistry

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Editors:
Prof. Tanja Gulder, Universität Leipzig and Universität des Saarlandes
Prof. Joanna Wencel-Delord, Universität Würzburg and Université de Strasbourg/Université de Haute Alsace
 
Hypervalent halogen chemistry has recently evolved from a chemical curiosity to a widespread versatile synthetic methodology that is not limited to simple oxidation reactions anymore. In this thematic issue, we will cover the novel concepts and the latest developments in hypervalent halogen chemistry, in particular those addressing new reactivities, catalytic and/or enantioselective transformations, electrochemistry, as well as photochemistry.

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SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

  • Julien Borrel and
  • Jerome Waser

Beilstein J. Org. Chem. 2024, 20, 701–713, doi:10.3762/bjoc.20.64

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Published 03 Apr 2024

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

  • Ke Jiang,
  • Cheng Pan,
  • Limin Wang,
  • Hao-Yang Wang and
  • Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

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Published 18 Apr 2024

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

  • Jun Kikuchi,
  • Roi Nakajima and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2024, 20, 891–897, doi:10.3762/bjoc.20.79

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Published 22 Apr 2024

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

  • Naoki Miyamoto,
  • Daichi Koseki,
  • Kohei Sumida,
  • Elghareeb E. Elboray,
  • Naoko Takenaga,
  • Ravi Kumar and
  • Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

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Published 03 May 2024

Oxidative hydrolysis of aliphatic bromoalkenes: scope study and reactivity insights

  • Amol P. Jadhav and
  • Claude Y. Legault

Beilstein J. Org. Chem. 2024, 20, 1286–1291, doi:10.3762/bjoc.20.111

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Published 03 Jun 2024

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

  • Akanksha Chhikara,
  • Fan Wu,
  • Navdeep Kaur,
  • Prabagar Baskaran,
  • Alex M. Nguyen,
  • Zhichang Yin,
  • Anthony H. Pham and
  • Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

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Published 24 Jun 2024

A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors

  • Nicole Javaly,
  • Theresa M. McCormick and
  • David R. Stuart

Beilstein J. Org. Chem. 2024, 20, 1428–1435, doi:10.3762/bjoc.20.125

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Published 27 Jun 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

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Published 28 Jun 2024

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl2 and NH4SCN/KSeCN

  • Jialiang Wu,
  • Haofeng Shi,
  • Xuemin Li,
  • Jiaxin He,
  • Chen Zhang,
  • Fengxia Sun and
  • Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

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Published 28 Jun 2024

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

  • Christopher Mairhofer,
  • David Naderer and
  • Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

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Published 05 Jul 2024

Divergent role of PIDA and PIFA in the AlX3 (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study

  • Kevin A. Juárez-Ornelas,
  • Manuel Solís-Hernández,
  • Pedro Navarro-Santos,
  • J. Oscar C. Jiménez-Halla and
  • César R. Solorio-Alvarado

Beilstein J. Org. Chem. 2024, 20, 1580–1589, doi:10.3762/bjoc.20.141

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Published 15 Jul 2024

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ3-iodanes

  • Thomas J. Kuczmera,
  • Pim Puylaert and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

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Published 19 Jul 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

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Published 29 Jul 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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Published 07 Aug 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

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Published 11 Sep 2024

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

  • Dominik L. Reinhard,
  • Anna Schmidt,
  • Marc Sons,
  • Julian Wolf,
  • Elric Engelage and
  • Stefan M. Huber

Beilstein J. Org. Chem. 2024, 20, 2401–2407, doi:10.3762/bjoc.20.204

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Published 23 Sep 2024

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

  • Smaher E. Butt,
  • Konrad Kepski,
  • Jean-Marc Sotiropoulos and
  • Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

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Published 30 Sep 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

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Review
Published 13 Nov 2024

Structure and thermal stability of phosphorus-iodonium ylids

  • Andrew Greener,
  • Stephen P. Argent,
  • Coby J. Clarke and
  • Miriam L. O’Duill

Beilstein J. Org. Chem. 2024, 20, 2931–2939, doi:10.3762/bjoc.20.245

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Published 14 Nov 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

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Published 28 Nov 2024

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

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Published 04 Dec 2024
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