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Literature DB >> 26676401

An Improved System for the Aqueous Lipshutz-Negishi Cross-Coupling of Alkyl Halides with Aryl Electrophiles.

Vasudev R Bhonde¹, Brian T O'Neill², Stephen L Buchwald³.

Abstract

The development of a palladacyclic precatalyst supported by a new biaryl(dialkyl)phosphine ligand (VPhos) in combination with octanoic acid/sodium octanoate as a simple and effective surfactant system provided an improved catalyst system for the rapid construction of a broad spectrum of alkylated scaffolds from alkyl zinc reagents generated in situ.

Entities: Chemical

Keywords: alkyl zinc reagents; cross-coupling; micelles; palladium precatalysts; surfactants

Mesh：

Substances：
Halogens
Water

Year: 2015 PMID： 26676401 DOI： 10.1002/anie.201509341

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

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Cited

13 in total

1. Metallaphotoredox-Catalyzed Cross-Electrophile C_sp³-C_sp³ Coupling of Aliphatic Bromides.

Authors: Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan
Journal: J Am Chem Soc Date: 2018-12-10 Impact factor: 15.419

2. Well-defined nickel and palladium precatalysts for cross-coupling.

Authors: Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal: Nat Rev Chem Date: 2017-03-01 Impact factor: 34.035

3. Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors: Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal: J Am Chem Soc Date: 2020-06-26 Impact factor: 15.419

4. A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors: Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2017-05-16 Impact factor: 15.336

5. Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling.

Authors: Patricia Zhang; Chi Chip Le; David W C MacMillan
Journal: J Am Chem Soc Date: 2016-06-22 Impact factor: 15.419

6. Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling.

Authors: James J Perkins; Valerie W Shurtleff; Alayna M Johnson; Abdellatif El Marrouni
Journal: ACS Med Chem Lett Date: 2021-03-08 Impact factor: 4.345

An Improved System for the Aqueous Lipshutz-Negishi Cross-Coupling of Alkyl Halides with Aryl Electrophiles.

1. Metallaphotoredox-Catalyzed Cross-Electrophile C_sp³-C_sp³ Coupling of Aliphatic Bromides.

2. Well-defined nickel and palladium precatalysts for cross-coupling.

3. Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

4. A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

5. Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling.

6. Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling.

7. Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence.

8. Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling.

9. A mild catalytic system for radical conjugate addition of nitrogen heterocycles.

10. Cobalt-Catalyzed C(sp²)-C(sp³) Suzuki-Miyaura Cross Coupling.