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Literature DB >> 11009388

Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate.

Abstract

Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-n-butyl thiol esters were most effective in this cross-coupling.

Entities: Chemical

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Year: 2000 PMID： 11009388 DOI： 10.1021/ol000231a

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Catalytic Properties of Unsupported Palladium Nanoparticle Surfaces Capped with Small Organic Ligands.

Authors: Diego J Gavia; Young-Seok Shon
Journal: ChemCatChem Date: 2015-03-01 Impact factor: 5.686

2. Mobilizing Cu(I) for carbon-carbon bond forming catalysis in the presence of thiolate. Chemical mimicking of metallothioneins.

Authors: Zhihui Zhang; Matthew G Lindale; Lanny S Liebeskind
Journal: J Am Chem Soc Date: 2011-03-30 Impact factor: 15.419

3. Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

Authors: Baris Yucel; Patrick J Walsh
Journal: Adv Synth Catal Date: 2014-11-24 Impact factor: 5.837

4. Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture.

Authors: Chengwei Liu; Michal Szostak
Journal: Org Chem Front Date: 2021-06-22 Impact factor: 5.456

5. Thiomaleic anhydride: a convenient building block for the synthesis of alpha-substituted gamma- and delta-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation.

Authors: David Crich; Md Yeajur Rahaman
Journal: J Org Chem Date: 2009-09-04 Impact factor: 4.354

Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate.

1. Catalytic Properties of Unsupported Palladium Nanoparticle Surfaces Capped with Small Organic Ligands.

2. Mobilizing Cu(I) for carbon-carbon bond forming catalysis in the presence of thiolate. Chemical mimicking of metallothioneins.

3. Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

4. Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture.

5. Thiomaleic anhydride: a convenient building block for the synthesis of alpha-substituted gamma- and delta-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation.

Review 6. Late stage C-H functionalization via chalcogen and pnictogen salts.

7. Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles.

8. Azulenesulfonium Salts: Accessible, Stable, and Versatile Reagents for Cross-Coupling.