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Literature DB >> 24341523

A general strategy for organocatalytic activation of C-H bonds via photoredox catalysis: direct arylation of benzylic ethers.

Katrine Qvortrup¹, Danica A Rankic, David W C MacMillan.

Abstract

Direct C-H functionalization and arylation of benzyl ethers has been accomplished via photoredox organocatalysis. The productive merger of a thiol catalyst and a commercially available iridium photoredox catalyst in the presence of household light directly affords benzylic arylation products in good to excellent yield. The utility of this methodology is further demonstrated in direct arylation of 2,5-dihydrofuran to form a single regioisomer.

Entities: Chemical Species

Mesh：

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Year: 2013 PMID： 24341523 PMCID： PMC3988471 DOI： 10.1021/ja411596q

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

18 in total

Review 1. Proton-coupled electron transfer: a reaction chemist's view.

Authors: James M Mayer
Journal: Annu Rev Phys Chem Date: 2004 Impact factor: 12.703

2. Organometallic chemistry: C-H activation.

Authors: Robert G Bergman
Journal: Nature Date: 2007-03-22 Impact factor: 49.962

3. Catalytic ketyl-olefin cyclizations enabled by proton-coupled electron transfer.

Authors: Kyle T Tarantino; Peng Liu; Robert R Knowles
Journal: J Am Chem Soc Date: 2013-06-28 Impact factor: 15.419

4. Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity.

Authors: Andrew McNally; Christopher K Prier; David W C MacMillan
Journal: Science Date: 2011-11-25 Impact factor: 47.728

5. Thiyl radical mediated racemization of nonactivated aliphatic amines.

Authors: Stéphanie Escoubet; Stéphane Gastaldi; Nicolas Vanthuyne; Gérard Gil; Didier Siri; Michèle P Bertrand
Journal: J Org Chem Date: 2006-09-15 Impact factor: 4.354

Review 6. Understanding and exploiting C-H bond activation.

Authors: Jay A Labinger; John E Bercaw
Journal: Nature Date: 2002-05-30 Impact factor: 49.962

7. C-H bond functionalization in complex organic synthesis.

Authors: Kamil Godula; Dalibor Sames
Journal: Science Date: 2006-04-07 Impact factor: 47.728

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

Authors: Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal: J Org Chem Date: 2012-11-12 Impact factor: 4.354

9. Photoredox activation for the direct β-arylation of ketones and aldehydes.

Authors: Michael T Pirnot; Danica A Rankic; David B C Martin; David W C MacMillan
Journal: Science Date: 2013-03-29 Impact factor: 47.728

10. Photoreversible patterning of biomolecules within click-based hydrogels.

Authors: Cole A DeForest; Kristi S Anseth
Journal: Angew Chem Int Ed Engl Date: 2011-12-08 Impact factor: 15.336

37 in total

1. O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

Authors: Jenna L Jeffrey; Jack A Terrett; David W C MacMillan
Journal: Science Date: 2015-08-27 Impact factor: 47.728

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

Authors: James J Devery; Corey R J Stephenson
Journal: Nature Date: 2015-03-05 Impact factor: 49.962

3. Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations.

Authors: Yifan Deng; Qi Liu; Amos B Smith
Journal: J Am Chem Soc Date: 2017-07-10 Impact factor: 15.419

A general strategy for organocatalytic activation of C-H bonds via photoredox catalysis: direct arylation of benzylic ethers.

Review 1. Proton-coupled electron transfer: a reaction chemist's view.

2. Organometallic chemistry: C-H activation.

3. Catalytic ketyl-olefin cyclizations enabled by proton-coupled electron transfer.

4. Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity.

5. Thiyl radical mediated racemization of nonactivated aliphatic amines.

Review 6. Understanding and exploiting C-H bond activation.

7. C-H bond functionalization in complex organic synthesis.

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

9. Photoredox activation for the direct β-arylation of ketones and aldehydes.

10. Photoreversible patterning of biomolecules within click-based hydrogels.

1. O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

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

3. Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations.

4. A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis.

5. Catalytic Alkene Difunctionalization via Imidate Radicals.

6. Direct, enantioselective α-alkylation of aldehydes using simple olefins.

Review 7. Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities.

8. Direct C(sp³)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals.

9. Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides.

10. Native functionality in triple catalytic cross-coupling: sp³ C-H bonds as latent nucleophiles.