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Literature DB >> 27065751

A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

Linlin Qin¹, Bao Hu², Kiel D Neumann¹, Ethan J Linstad¹, Katelyenn McCauley¹, Jordan Veness¹, Jayson J Kempinger¹, Stephen G DiMagno¹.

Abstract

Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable, synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

Entities: Chemical Disease Gene

Keywords: Selectfluor™; aryl iodides; diaryliodonium salts; iodane synthesis; oxidation

Year: 2015 PMID： 27065751 PMCID： PMC4824678 DOI： 10.1002/ejoc.201500986

Source DB: PubMed Journal: European J Org Chem ISSN： 1099-0690

42 in total

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2. A chiral hypervalent iodine(III) reagent for enantioselective dearomatization of phenols.

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Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride.

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Journal: Org Lett Date: 1999-08-26 Impact factor: 6.005

4. Enantioselective Kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine(III) species.

Authors: Muhammet Uyanik; Takeshi Yasui; Kazuaki Ishihara
Journal: Angew Chem Int Ed Engl Date: 2010-03-15 Impact factor: 15.336

5. Fast and high-yield microreactor syntheses of ortho-substituted [(18)F]fluoroarenes from reactions of [(18)F]fluoride ion with diaryliodonium salts.

Authors: Joong-Hyun Chun; Shuiyu Lu; Yong-Sok Lee; Victor W Pike
Journal: J Org Chem Date: 2010-05-21 Impact factor: 4.354

6. Reaction of arenes with iodine in the presence of potassium peroxodisulfate in trifluoroacetic acid. Direct and simple synthesis of diaryliodonium triflates.

Authors: Md Delwar Hossain; Yasuyuki Ikegami; Tsugio Kitamura
Journal: J Org Chem Date: 2006-12-22 Impact factor: 4.354

7. Diaryliodonium salts: a journey from obscurity to fame.

Authors: Eleanor A Merritt; Berit Olofsson
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

8. Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides.

Authors: Marcin Bielawski; David Aili; Berit Olofsson
Journal: J Org Chem Date: 2008-05-28 Impact factor: 4.354

9. Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride.

Authors: Tobias L Ross; Johannes Ermert; Carsten Hocke; Heinz H Coenen
Journal: J Am Chem Soc Date: 2007-05-31 Impact factor: 15.419

10. Reactions of hypervalent iodine reagents with palladium: mechanisms and applications in organic synthesis.

Authors: Nicholas R Deprez; Melanie S Sanford
Journal: Inorg Chem Date: 2007-03-19 Impact factor: 5.165

6 in total

1. Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines.

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Journal: Angew Chem Int Ed Engl Date: 2016-08-24 Impact factor: 15.336