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Literature DB >> 24090404

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

Enrico T Nadres¹, Gerson Ivan Franco Santos, Dmitry Shabashov, Olafs Daugulis.

Abstract

The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp(2) and sp(3) C-H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in tert-amyl alcohol or water solvent at 100-140 °C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. The picolinic acid auxiliary is used for amine γ-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid β-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.

Entities: Chemical Gene

Mesh：

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Year: 2013 PMID： 24090404 PMCID： PMC3829615 DOI： 10.1021/jo4013628

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

73 in total

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

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

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. Cobalt-catalyzed ortho-alkylation of secondary benzamide with alkyl chloride through directed C-H bond activation.

Authors: Quan Chen; Laurean Ilies; Eiichi Nakamura
Journal: J Am Chem Soc Date: 2010-12-15 Impact factor: 15.419

4. β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation.

Authors: Rui Shang; Laurean Ilies; Arimasa Matsumoto; Eiichi Nakamura
Journal: J Am Chem Soc Date: 2013-04-16 Impact factor: 15.419

5. Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance.

Authors: Yoshinori Aihara; Naoto Chatani
Journal: J Am Chem Soc Date: 2013-04-01 Impact factor: 15.419

6. Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system.

Authors: Lehao Huang; Qian Li; Chen Wang; Chenze Qi
Journal: J Org Chem Date: 2013-02-20 Impact factor: 4.354

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

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

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

3. Cobalt-catalyzed ortho-alkylation of secondary benzamide with alkyl chloride through directed C-H bond activation.

4. β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation.

5. Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance.

6. Palladium(II)-catalyzed regioselective arylation of naphthylamides with aryl iodides utilizing a quinolinamide bidentate system.

7. meta-Selective C-H bond alkylation with secondary alkyl halides.

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

9. Copper-promoted sulfenylation of sp2 C-H bonds.

10. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

1. Ligand-Enabled Arylation of γ-C-H Bonds.

2. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

3. Bidentate, monoanionic auxiliary-directed functionalization of carbon-hydrogen bonds.

4. Synthesis and Properties of "Sandwich" Diimine-Coinage Metal Ethylene Complexes.

5. Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp³ C-H bonds.

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

7. A Mixed-Ligand Chiral Rhodium(II) Catalyst Enables the Enantioselective Total Synthesis of Piperarborenine B.

8. Enantioselective ortho-C-H cross-coupling of diarylmethylamines with organoborons.

9. Ligand-enabled γ-C-H olefination and carbonylation: construction of β-quaternary carbon centers.

10. Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds.