Literature DB >> 24063629

Cu-catalyzed fluorination of diaryliodonium salts with KF.

Naoko Ichiishi1, Allan J Canty, Brian F Yates, Melanie S Sanford.   

Abstract

A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a Cu(I)/Cu(III) catalytic cycle.

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Year:  2013        PMID： 24063629      PMCID： PMC4096328          DOI： 10.1021/ol4025716

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

1.  Fluoride-Promoted Ligand Exchange in Diaryliodonium Salts.

Authors:  Bijia Wang; Ronald L Cerny; Shriharsha Uppaluri; Jayson J Kempinger; Stephen G Dimagno
Journal:  J Fluor Chem       Date:  2010-11-01       Impact factor: 2.050

2.  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

3.  Regiospecific reductive elimination from diaryliodonium salts.

Authors:  Bijia Wang; Joseph W Graskemper; Linlin Qin; Stephen G DiMagno
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-01       Impact factor: 15.336

4.  Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

Authors:  Shaolin Zhu; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2012-06-22       Impact factor: 15.419

5.  Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation.

Authors:  Bo Chen; Xue-Long Hou; Yu-Xue Li; Yun-Dong Wu
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

6.  Copper-mediated fluorination of arylboronate esters. Identification of a copper(III) fluoride complex.

Authors:  Patrick S Fier; Jingwei Luo; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-02-05       Impact factor: 15.419

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.  Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions.

Authors:  Robert J Phipps; Neil P Grimster; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

Review 9.  Carbon-fluorine bond formation.

Authors:  Takeru Furuya; Christian A Kuttruff; Tobias Ritter
Journal:  Curr Opin Drug Discov Devel       Date:  2008-11

10.  Copper-catalyzed, directing group-assisted fluorination of arene and heteroarene C-H bonds.

Authors:  Thanh Truong; Kristine Klimovica; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419
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  30 in total

1.  Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Authors:  Ruth Dorel; Philip Boehm; Daniel P Schwinger; John F Hartwig
Journal:  Chemistry       Date:  2020-01-28       Impact factor: 5.236

2.  The new breed of cutting-edge catalysts.

Authors:  XiaoZhi Lim
Journal:  Nature       Date:  2016-09-08       Impact factor: 49.962

3.  Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

Authors:  Mohammad B Khaled; Roukaya K El Mokadem; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

4.  Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts.

Authors:  François Guérard; Yong-Sok Lee; Kwamena Baidoo; Jean-François Gestin; Martin W Brechbiel
Journal:  Chemistry       Date:  2016-06-15       Impact factor: 5.236

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

Authors:  Zheliang Yuan; Ran Cheng; Pinhong Chen; Guosheng Liu; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-24       Impact factor: 15.336

6.  Late-stage [18F]Fluorination: New Solutions to Old Problems.

Authors:  Allen F Brooks; Joseph J Topczewski; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

7.  Rapid Cu-Catalyzed [211At]Astatination and [125I]Iodination of Boronic Esters at Room Temperature.

Authors:  Sean W Reilly; Mehran Makvandi; Kuiying Xu; Robert H Mach
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

8.  Photocatalytic C-F Reduction and Functionalization.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

9.  Synthesis of high-molar-activity [18F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

Authors:  Andrew V Mossine; Sean S Tanzey; Allen F Brooks; Katarina J Makaravage; Naoko Ichiishi; Jason M Miller; Bradford D Henderson; Thomas Erhard; Christian Bruetting; Marc B Skaddan; Melanie S Sanford; Peter J H Scott
Journal:  Nat Protoc       Date:  2020-04-08       Impact factor: 13.491

10.  C(sp³)-¹⁸F bond formation by transition-metal-based [¹⁸F]fluorination.

Authors:  Steven H Liang; Neil Vasdev
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-22       Impact factor: 15.336
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