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Literature DB >> 22229949

A new reagent for direct difluoromethylation.

Yuta Fujiwara¹, Janice A Dixon, Rodrigo A Rodriguez, Ryan D Baxter, Darryl D Dixon, Michael R Collins, Donna G Blackmond, Phil S Baran.

Abstract

Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO(2)CF(2)H)(2), DFMS) for the innate difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated π-systems and thiols. Regiochemical comparisons suggest that the CF(2)H radical generated from the new reagent possesses nucleophilic character.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2012 PMID： 22229949 PMCID： PMC3269891 DOI： 10.1021/ja211422g

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

10 in total

1. A designed P1 cysteine mimetic for covalent and non-covalent inhibitors of HCV NS3 protease.

Authors: Frank Narjes; Konrad F Koehler; Uwe Koch; Benjamin Gerlach; Stefania Colarusso; Christian Steinkühler; Mirko Brunetti; Sergio Altamura; Raffaele De Francesco; Victor G Matassa
Journal: Bioorg Med Chem Lett Date: 2002-02-25 Impact factor: 2.823

2. Introduction: Fluorine Chemistry.

Authors: Bruce E. Smart
Journal: Chem Rev Date: 1996-08-01 Impact factor: 60.622

3. A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.

Authors: Kenichi Fujikawa; Yasutaka Fujioka; Akira Kobayashi; Hideki Amii
Journal: Org Lett Date: 2011-09-28 Impact factor: 6.005

4. Innate and guided C-H functionalization logic.

Authors: Tobias Brückl; Ryan D Baxter; Yoshihiro Ishihara; Phil S Baran
Journal: Acc Chem Res Date: 2011-10-21 Impact factor: 22.384

5. Synthesis and biological evaluation of novel analogues of the pan class I phosphatidylinositol 3-kinase (PI3K) inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474).

Authors: Gordon W Rewcastle; Swarna A Gamage; Jack U Flanagan; Raphael Frederick; William A Denny; Bruce C Baguley; Philip Kestell; Ripudaman Singh; Jackie D Kendall; Elaine S Marshall; Claire L Lill; Woo-Jeong Lee; Sharada Kolekar; Christina M Buchanan; Stephen M F Jamieson; Peter R Shepherd
Journal: J Med Chem Date: 2011-09-27 Impact factor: 7.446

6. Synopsis of some recent tactical application of bioisosteres in drug design.

Authors: Nicholas A Meanwell
Journal: J Med Chem Date: 2011-03-17 Impact factor: 7.446

7. Selective difluoromethylation and monofluoromethylation reactions.

Authors: Jinbo Hu; Wei Zhang; Fei Wang
Journal: Chem Commun (Camb) Date: 2009-10-30 Impact factor: 6.222

8. Innate C-H trifluoromethylation of heterocycles.

Authors: Yining Ji; Tobias Brueckl; Ryan D Baxter; Yuta Fujiwara; Ian B Seiple; Shun Su; Donna G Blackmond; Phil S Baran
Journal: Proc Natl Acad Sci U S A Date: 2011-08-15 Impact factor: 11.205

9. Synthesis of celecoxib analogues possessing a N-difluoromethyl-1,2-dihydropyrid-2-one 5-lipoxygenase pharmacophore: biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity.

Authors: Morshed A Chowdhury; Khaled R A Abdellatif; Ying Dong; Dipankar Das; Mavanur R Suresh; Edward E Knaus
Journal: J Med Chem Date: 2009-03-26 Impact factor: 7.446

Review 10. Carbon-fluorine bond formation.

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

10 in total

54 in total

10. Optimized Synthesis of a Pentafluoro-gem-diol and Conversion to a CF₂Br-Glucopyranose through Trifluoroacetate-Release and Halogenation.

Authors: Robert A Hazlitt; Jinu P John; Que-Lynn Tran; David A Colby
Journal: Tetrahedron Lett Date: 2016-03-19 Impact factor: 2.415

A new reagent for direct difluoromethylation.

1. A designed P1 cysteine mimetic for covalent and non-covalent inhibitors of HCV NS3 protease.

2. Introduction: Fluorine Chemistry.

3. A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.

4. Innate and guided C-H functionalization logic.

5. Synthesis and biological evaluation of novel analogues of the pan class I phosphatidylinositol 3-kinase (PI3K) inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474).

6. Synopsis of some recent tactical application of bioisosteres in drug design.

7. Selective difluoromethylation and monofluoromethylation reactions.

8. Innate C-H trifluoromethylation of heterocycles.

9. Synthesis of celecoxib analogues possessing a N-difluoromethyl-1,2-dihydropyrid-2-one 5-lipoxygenase pharmacophore: biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity.

Review 10. Carbon-fluorine bond formation.

1. Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

2. Selective C-F Functionalization of Unactivated Trifluoromethylarenes.

3. Copper-mediated difluoromethylation of aryl and vinyl iodides.

4. Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

5. Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium.

6. Bioconjugation by native chemical tagging of C-H bonds.

7. Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Review 8. Chemo- and site-selective derivatizations of natural products enabling biological studies.

9. Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.

10. Optimized Synthesis of a Pentafluoro-gem-diol and Conversion to a CF₂Br-Glucopyranose through Trifluoroacetate-Release and Halogenation.