Journal article
An Improved System for the Aqueous Lipshutz–Negishi Cross‐Coupling of Alkyl Halides with Aryl Electrophiles
Angewandte Chemie (International ed.), Vol.55(5), pp.1849-1853
01/26/2016
DOI: 10.1002/anie.201509341
PMID: 26676401
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.
Happy to get its feet wet: VPhos was developed as a hybrid ligand incorporating structural elements of existing ligands for improved activity in the micelle‐enhanced palladium‐catalyzed cross‐coupling of non‐aromatic O‐ and N‐heterocyclic alkyl bromides with (hetero)aryl halides (see scheme). The Pd/VPhos catalyst (5 mol %) and a simple surfactant system based on octanoic acid enabled the efficient synthesis of a broad range of alkylated (hetero)arenes.
Details
- Title: Subtitle
- An Improved System for the Aqueous Lipshutz–Negishi Cross‐Coupling of Alkyl Halides with Aryl Electrophiles
- Creators
- Vasudev R Bhonde - Massachusetts Institute of TechnologyBrian T O'Neill - Pfizer Worldwide Research and DevelopmentStephen L Buchwald - Massachusetts Institute of Technology
- Resource Type
- Journal article
- Publication Details
- Angewandte Chemie (International ed.), Vol.55(5), pp.1849-1853
- DOI
- 10.1002/anie.201509341
- PMID
- 26676401
- ISSN
- 1433-7851
- eISSN
- 1521-3773
- Number of pages
- 5
- Grant note
- World Wide Medicinal Chemistry and External R&D Innovation at Pfizer
- Language
- English
- Date published
- 01/26/2016
- Academic Unit
- Endocrinology and Metabolism; Internal Medicine
- Record Identifier
- 9984094551402771
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