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

Vasudev R Bhonde; Brian T O'Neill; Stephen L Buchwald

doi:10.1002/anie.201509341

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

Angew Chem Int Ed Engl. 2016 Jan 26;55(5):1849-53. doi: 10.1002/anie.201509341. Epub 2015 Dec 16.

Authors

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

Affiliations

¹ Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.
² Pfizer Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development, Groton, CT, 06340, USA.
³ Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA. sbuchwal@mit.edu.

PMID: 26676401
DOI: 10.1002/anie.201509341

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.

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

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Halogens / chemistry*
Water / chemistry

Substances

Halogens
Water