Literature DB >> 26990693

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

Enxuan Zhang1, Jiaze Tang2, Suhua Li3, Peng Wu4, John E Moses5, K Barry Sharpless6.   

Abstract

A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2 F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Suzuki reaction; chemoselectivity; cross-coupling reactions; fluorosulfates; palladium; polysubstituted pyridine

Mesh：

Substances：

Year:  2016        PMID： 26990693      PMCID： PMC4929982          DOI： 10.1002/chem.201600167

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  11 in total

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Journal:  Org Lett       Date:  2015-04-09       Impact factor: 6.005

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Authors:  Jiajia Dong; Larissa Krasnova; M G Finn; K Barry Sharpless
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6.  2-Amino-4,6-diarylpyridines as novel ligands for the estrogen receptor.

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7.  A practical synthesis of a COX-2-specific inhibitor.

Authors:  I W Davies; J F Marcoux; E G Corley; M Journet; D W Cai; M Palucki; J Wu; R D Larsen; K Rossen; P J Pye; L DiMichele; P Dormer; P J Reider
Journal:  J Org Chem       Date:  2000-12-15       Impact factor: 4.354

Review 8.  Single dose oral etoricoxib for acute postoperative pain in adults.

Authors:  Rachel Clarke; Sheena Derry; R Andrew Moore
Journal:  Cochrane Database Syst Rev       Date:  2014-05-08

9.  2-Pyridinyl-3-(4-methylsulfonyl)phenylpyridines: selective and orally active cyclooxygenase-2 inhibitors.

Authors:  R W Friesen; C Brideau; C C Chan; S Charleson; D Deschênes; D Dubé; D Ethier; R Fortin; J Y Gauthier; Y Girard; R Gordon; G M Greig; D Riendeau; C Savoie; Z Wang; E Wong; D Visco; L J Xu; R N Young
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  6 in total

1.  SuFEx Chemistry of Thionyl Tetrafluoride (SOF4 ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.

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4.  Site-Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO2 F) Enabled by an Air-Stable PdI Dimer.

Authors:  Marvin Mendel; Indrek Kalvet; Daniel Hupperich; Guillaume Magnin; Franziska Schoenebeck
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5.  Continuous flow synthesis of aryl aldehydes by Pd-catalyzed formylation of phenol-derived aryl fluorosulfonates using syngas.

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6.  Rapid and column-free syntheses of acyl fluorides and peptides using ex situ generated thionyl fluoride.

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  6 in total

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