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Literature DB >> 24975840

The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

Abstract

tert-Butoxyacetylene is shown to undergo Sonogashira coupling with aryl iodides to yield aryl-substituted tert-butyl ynol ethers. These intermediates participate in a [1,5]-hydride shift, which results in the extrusion of isobutylene and the generation of aryl ketenes. The ketenes are trapped in situ with multiple nucleophiles or undergo electrocyclic ring closure to yield hydroxynaphthalenes and quinolines.

Entities: Chemical Disease Gene

Keywords: arenes; cross-coupling; ketenes; palladium; synthetic methods

Mesh：

Substances：

Year: 2014 PMID： 24975840 PMCID： PMC4134717 DOI： 10.1002/anie.201405036

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

19 in total

1. Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata.

Authors: Michele Badioli; Roberto Ballini; Massimo Bartolacci; Giovanna Bosica; Elisabetta Torregiani; Enrico Marcantoni
Journal: J Org Chem Date: 2002-12-13 Impact factor: 4.354

2. Anodic oxidation and organocatalysis: direct regio- and stereoselective access to meta-substituted anilines by alpha-arylation of aldehydes.

Authors: Kim L Jensen; Patrick T Franke; Lasse T Nielsen; Kim Daasbjerg; Karl Anker Jørgensen
Journal: Angew Chem Int Ed Engl Date: 2010 Impact factor: 15.336

3. Intermolecular and selective synthesis of 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.

Authors: Paul W Davies; Alex Cremonesi; Lidia Dumitrescu
Journal: Angew Chem Int Ed Engl Date: 2011-07-26 Impact factor: 15.336

4. Sulfur(IV)-mediated transformations: from ylide transfer to metal-free arylation of carbonyl compounds.

Authors: Xueliang Huang; Mahendra Patil; Christophe Farès; Walter Thiel; Nuno Maulide
Journal: J Am Chem Soc Date: 2013-05-03 Impact factor: 15.419

5. Aerobic, transition-metal-free, direct, and regiospecific mono-α-arylation of ketones: synthesis and mechanism by DFT calculations.

Authors: Qing-Long Xu; Hongyin Gao; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal: J Am Chem Soc Date: 2013-09-11 Impact factor: 15.419

6. Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

Authors: Aurélien Bigot; Alice E Williamson; Matthew J Gaunt
Journal: J Am Chem Soc Date: 2011-08-17 Impact factor: 15.419

7. Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.

Authors: Hosea M Nelson; Jonny R Gordon; Scott C Virgil; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2013-05-16 Impact factor: 15.336

The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

1. Addition of organocerium reagents to morpholine amides: synthesis of important pheromone components of Achaea janata.

2. Anodic oxidation and organocatalysis: direct regio- and stereoselective access to meta-substituted anilines by alpha-arylation of aldehydes.

3. Intermolecular and selective synthesis of 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3+2] cycloaddition.

4. Sulfur(IV)-mediated transformations: from ylide transfer to metal-free arylation of carbonyl compounds.

5. Aerobic, transition-metal-free, direct, and regiospecific mono-α-arylation of ketones: synthesis and mechanism by DFT calculations.

6. Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

7. Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.

8. Rhodium-catalyzed oxygenative addition to terminal alkynes for the synthesis of esters, amides, and carboxylic acids.

9. Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin α.

10. Platinum-catalyzed oxoarylations of ynamides with nitrones.

1. A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

2. Inhibitors of 15-Prostaglandin Dehydrogenase To Potentiate Tissue Repair.

3. Preparation of 3-hydroxyquinolines from direct oxidation of dihydroquinolinium salts.