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Literature DB >> 22047138

Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis.

Dipannita Kalyani¹, Kate B McMurtrey, Sharon R Neufeldt, Melanie S Sanford.

Abstract

This communication describes the development of a room-temperature ligand-directed C-H arylation reaction using aryldiazonium salts. This was achieved by the successful merger of palladium-catalyzed C-H functionalization and visible-light photoredox catalysis. The new method is general for a variety of directing groups and tolerates many common functional groups.

Entities: Chemical Species

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Year: 2011 PMID： 22047138 PMCID： PMC3222896 DOI： 10.1021/ja208068w

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

22 in total

1. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors: Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal: Chem Rev Date: 2002-05 Impact factor: 60.622

2. Visible light photoredox catalysis: applications in organic synthesis.

Authors: Jagan M R Narayanam; Corey R J Stephenson
Journal: Chem Soc Rev Date: 2010-06-08 Impact factor: 54.564

Review 3. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors: Dino Alberico; Mark E Scott; Mark Lautens
Journal: Chem Rev Date: 2007-01 Impact factor: 60.622

Review 4. Recent advances in aryl-aryl bond formation by direct arylation.

Authors: Gerard P McGlacken; Lorraine M Bateman
Journal: Chem Soc Rev Date: 2009-05-22 Impact factor: 54.564

Review 5. Towards mild metal-catalyzed C-H bond activation.

Authors: Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal: Chem Soc Rev Date: 2011-06-10 Impact factor: 54.564

6. Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

Authors: Kami L Hull; Erica L Lanni; Melanie S Sanford
Journal: J Am Chem Soc Date: 2006-11-01 Impact factor: 15.419

7. Palladium(II)-catalyzed C-H bond arylation of electron-deficient arenes at room temperature.

Authors: Matthew J Tredwell; Moises Gulias; Nadine Gaunt Bremeyer; Carin C C Johansson; Beatrice S L Collins; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2010-12-22 Impact factor: 15.336

8. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Authors: Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford
Journal: J Am Chem Soc Date: 2005-05-25 Impact factor: 15.419

9. O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization.

Authors: Sharon R Neufeldt; Melanie S Sanford
Journal: Org Lett Date: 2010-02-05 Impact factor: 6.005

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors: Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

85 in total

1. Metallaphotoredox-Catalyzed Cross-Electrophile C_sp³-C_sp³ Coupling of Aliphatic Bromides.

Authors: Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan
Journal: J Am Chem Soc Date: 2018-12-10 Impact factor: 15.419

2. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

Authors: Yingda Ye; Melanie S Sanford
Journal: J Am Chem Soc Date: 2012-05-24 Impact factor: 15.419

3. Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.

Authors: Sharon R Neufeldt; Melanie S Sanford
Journal: Adv Synth Catal Date: 2012-12-14 Impact factor: 5.837

Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis.

1. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

2. Visible light photoredox catalysis: applications in organic synthesis.

Review 3. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Review 4. Recent advances in aryl-aryl bond formation by direct arylation.

Review 5. Towards mild metal-catalyzed C-H bond activation.

6. Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

7. Palladium(II)-catalyzed C-H bond arylation of electron-deficient arenes at room temperature.

8. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

9. O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization.

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

1. Metallaphotoredox-Catalyzed Cross-Electrophile C_sp³-C_sp³ Coupling of Aliphatic Bromides.

2. Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

3. Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.

4. Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis.

5. Heck Reaction of Electronically Diverse Tertiary Alkyl Halides.

6. Catalysis: dual catalysis at the flick of a switch.

7. Visible-light sensitization of vinyl azides by transition-metal photocatalysis.

8. Transition metal photoredox catalysis of radical thiol-ene reactions.

9. Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

10. Asymmetric chiral ligand-directed alkene dioxygenation.