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Literature DB >> 20175511

Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Abstract

We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

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Year: 2010 PMID： 20175511 PMCID： PMC2841226 DOI： 10.1021/ja910900p

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

57 in total

1. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

Authors: B V Subba Reddy; Leleti Rajender Reddy; E J Corey
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

2. Synthesis of 3,4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: total synthesis of coralydine.

Authors: Manon Chaumontet; Riccardo Piccardi; Olivier Baudoin
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

3. A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage.

Authors: Fumitoshi Kakiuchi; Shintaro Kan; Kimitaka Igi; Naoto Chatani; Shinji Murai
Journal: J Am Chem Soc Date: 2003-02-19 Impact factor: 15.419

4. High-yielding palladium-catalyzed intramolecular alkane arylation: reaction development and mechanistic studies.

Authors: Marc Lafrance; Serge I Gorelsky; Keith Fagnou
Journal: J Am Chem Soc Date: 2007-11-07 Impact factor: 15.419

5. Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules.

Authors: Louis-Charles Campeau; Keith Fagnou
Journal: Chem Commun (Camb) Date: 2006-01-30 Impact factor: 6.222

6. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors: Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal: J Am Chem Soc Date: 2008-06-27 Impact factor: 15.419

10. Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

Authors: Jessica Z Chan; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Masayuki Wasa
Journal: J Am Chem Soc Date: 2020-09-11 Impact factor: 15.419

Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

1. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

2. Synthesis of 3,4-dihydroisoquinolines by a C(sp3)-H activation/electrocyclization strategy: total synthesis of coralydine.

3. A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage.

4. High-yielding palladium-catalyzed intramolecular alkane arylation: reaction development and mechanistic studies.

5. Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules.

6. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

7. Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

8. Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates.

9. Aromatic ortho-benzylation reveals an unexpected reductant.

10. Two methods for direct ortho-arylation of benzoic acids.

1. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

2. Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene.

3. Selective sp³ C-H alkylation via polarity-match-based cross-coupling.

4. Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

5. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

6. Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

7. γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

8. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

9. Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp² C-H Bonds.

10. Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.