Literature DB >> 15101768

Direct and convenient conversion of alcohols to fluorides.

Jingjun Yin1, Devin S Zarkowsky, David W Thomas, Matthew M Zhao, Mark A Huffman.   

Abstract

[reaction: see text] Directly mixing primary, secondary, and tertiary alcohols with nC(4)F(9)SO(2)F-NR(3)(HF)(3)-NR(3) in THF or MeCN results in convenient conversion to the corresponding fluorides in high yields. The readily available reagents are easy to handle, and the mild, almost neutral reaction conditions allow for excellent functional group compatibility. A NR(3)(HF)(3)/NR(3) ratio of </=1:2 gives the highest reactivity.

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Year:  2004        PMID: 15101768     DOI: 10.1021/ol049672a

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


  10 in total

1.  Development of α-GalCer Analogues with an α-Fluorocarbonyl Moiety as Th2-Selective Ligands of CD1d.

Authors:  Hyunsoo Kim; Heebum Song; Jun-Gyu Park; Dong-Sup Lee; Seung Bum Park
Journal:  ACS Med Chem Lett       Date:  2019-04-24       Impact factor: 4.345

2.  SulfoxFluor-enabled deoxyazidation of alcohols with NaN3.

Authors:  Junkai Guo; Xiu Wang; Chuanfa Ni; Xiaolong Wan; Jinbo Hu
Journal:  Nat Commun       Date:  2022-05-18       Impact factor: 17.694

3.  Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Orally Bioavailable and Brain Penetrant Mutant IDH1 Inhibitors.

Authors:  Qian Zhao; James R Manning; James Sutton; Abran Costales; Martin Sendzik; Cynthia M Shafer; Julian R Levell; Gang Liu; Thomas Caferro; Young Shin Cho; Mark Palermo; Gregg Chenail; Julia Dooley; Brian Villalba; Ali Farsidjani; Jinyun Chen; Stephanie Dodd; Ty Gould; Guiqing Liang; Kelly Slocum; Minying Pu; Brant Firestone; Joseph Growney; Tycho Heimbach; Raymond Pagliarini
Journal:  ACS Med Chem Lett       Date:  2018-06-11       Impact factor: 4.345

4.  Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling.

Authors:  Alexandre L'heureux; Francis Beaulieu; Christopher Bennett; David R Bill; Simon Clayton; François Laflamme; Mahmoud Mirmehrabi; Sam Tadayon; David Tovell; Michel Couturier
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

5.  Discovery and Evaluation of Clinical Candidate IDH305, a Brain Penetrant Mutant IDH1 Inhibitor.

Authors:  Young Shin Cho; Julian R Levell; Gang Liu; Thomas Caferro; James Sutton; Cynthia M Shafer; Abran Costales; James R Manning; Qian Zhao; Martin Sendzik; Michael Shultz; Gregg Chenail; Julia Dooley; Brian Villalba; Ali Farsidjani; Jinyun Chen; Raviraj Kulathila; Xiaoling Xie; Stephanie Dodd; Ty Gould; Guiqing Liang; Tycho Heimbach; Kelly Slocum; Brant Firestone; Minying Pu; Raymond Pagliarini; Joseph D Growney
Journal:  ACS Med Chem Lett       Date:  2017-09-18       Impact factor: 4.345

6.  An efficient synthesis of 4H-pyrano quinolinone derivatives catalysed by a versatile organocatalyst tetra-n-butylammonium fluoride and their pharmacological screening.

Authors:  Pratibha Prasad; Pratik G Shobhashana; Manish P Patel
Journal:  R Soc Open Sci       Date:  2017-11-29       Impact factor: 2.963

7.  One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.

Authors:  Alyn T Davies; John M Curto; Scott W Bagley; Michael C Willis
Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

8.  Photoredox-catalyzed aminofluorosulfonylation of unactivated olefins.

Authors:  Tao Zhong; Ji-Tao Yi; Zhi-Da Chen; Quan-Can Zhuang; Yong-Zhao Li; Gui Lu; Jiang Weng
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.825

9.  Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester.

Authors:  Antal Harsanyi; Graham Sandford; Dmitri S Yufit; Judith Ak Howard
Journal:  Beilstein J Org Chem       Date:  2014-05-22       Impact factor: 2.883

10.  Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture.

Authors:  Kavita Devi; Vinoth Rajendran; T M Rangarajan; Rishi Pal Singh; Prahlad C Ghosh; Manjula Singh
Journal:  Molecules       Date:  2018-05-14       Impact factor: 4.411

  10 in total

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