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Literature DB >> 23539600

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

Michael T Pirnot¹, Danica A Rankic, David B C Martin, David W C MacMillan.

Abstract

The direct β-activation of saturated aldehydes and ketones has long been an elusive transformation. We found that photoredox catalysis in combination with organocatalysis can lead to the transient generation of 5π-electron β-enaminyl radicals from ketones and aldehydes that rapidly couple with cyano-substituted aryl rings at the carbonyl β-position. This mode of activation is suitable for a broad range of carbonyl β-functionalization reactions and is amenable to enantioselective catalysis.

Entities: Chemical Disease Gene

Mesh：

Substances：
Aldehydes
Ketones

Year: 2013 PMID： 23539600 PMCID： PMC3723331 DOI： 10.1126/science.1232993

Source DB: PubMed Journal: Science ISSN： 0036-8075 Impact factor: 47.728

13 in total

1. Photochemical nucleophile-olefin combination, aromatic substitution reaction. Its synthetic development and mechanistic exploration.

Authors: Dino Mangion; Donald R Arnold
Journal: Acc Chem Res Date: 2002-05 Impact factor: 22.384

2. Palladium-catalyzed β arylation of carboxylic esters.

Authors: Alice Renaudat; Ludivine Jean-Gérard; Rodolphe Jazzar; Christos E Kefalidis; Eric Clot; Olivier Baudoin
Journal: Angew Chem Int Ed Engl Date: 2010-09-24 Impact factor: 15.336

Review 3. Asymmetric enamine catalysis.

Authors: Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

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. Organocatalytic enantioselective β-functionalization of aldehydes by oxidation of enamines and their application in cascade reactions.

Authors: Shi-Lei Zhang; He-Xin Xie; Jin Zhu; Hao Li; Xin-Shuai Zhang; Jian Li; Wei Wang
Journal: Nat Commun Date: 2011 Impact factor: 14.919

6. Palladium-catalyzed direct ethynylation of C(sp3)-H bonds in aliphatic carboxylic acid derivatives.

Authors: Yusuke Ano; Mamoru Tobisu; Naoto Chatani
Journal: J Am Chem Soc Date: 2011-08-03 Impact factor: 15.419

7. Rhodium-catalyzed 1,4-addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds: large accelerating effects of bases and ligands.

Authors: Ryoh Itooka; Yuki Iguchi; Norio Miyaura
Journal: J Org Chem Date: 2003-07-25 Impact factor: 4.354

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

1. Photochemical nucleophile-olefin combination, aromatic substitution reaction. Its synthetic development and mechanistic exploration.

2. Palladium-catalyzed β arylation of carboxylic esters.

Review 3. Asymmetric enamine catalysis.

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

5. Organocatalytic enantioselective β-functionalization of aldehydes by oxidation of enamines and their application in cascade reactions.

6. Palladium-catalyzed direct ethynylation of C(sp3)-H bonds in aliphatic carboxylic acid derivatives.

7. Rhodium-catalyzed 1,4-addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds: large accelerating effects of bases and ligands.

8. Efficient visible light photocatalysis of [2+2] enone cycloadditions.

9. The enantioselective organocatalytic 1,4-addition of electron-rich benzenes to alpha,beta-unsaturated aldehydes.

10. Copper-catalyzed enantioselective conjugate addition of grignard reagents to acyclic enones.

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

2. Carbene catalysis: An internal affair.

3. Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis.

4. β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis.

5. Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals.

6. Methylene C(sp³)-H Arylation of Aliphatic Ketones Using a Transient Directing Group.

7. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

8. Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization.

9. Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions.

10. Direct β-functionalization of cyclic ketones with aryl ketones via the merger of photoredox and organocatalysis.