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Amphiphilic Biaryl Monophosphine Ligands by Regioselective Sulfonation

07 December 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Amphiphilic ligands are valued for their ability to facilitate organometallic reactions in the presence of water. The regioselective sulfonation of a series of commercially available biaryl monophosphines to generate amphiphilic ligands is presented. In this one-step protocol, the temperature and addition of fuming sulfuric acid were carefully controlled to arrive at sulfonated biaryl monophosphine ligands in high yields with >95% regioselectivity without the need for chromatographic purification.

Keywords

sulfonation
biaryl monophosphine
water soluble ligand
ligand

Supplementary materials

Title
Description
Actions
Title
ChemRxiv Sulfonation SI 2020 12 05
Description
Actions

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Version History

Dec 07, 2020 Version 1

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License

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.13337471.v1
D O I: 10.26434/chemrxiv.13337471.v1 [opens in a new tab]

Funding

United States Department of Health and Human Services
361967
NATIONAL INSTITUTES OF HEALTH (NIH)
https://app.dimensions.ai/details/grant/grant.7587191 [opens in a new tab]
National Science Foundation (NSF)
Massachusetts Institute of Technology, Dean of Science Fellowship

Author’s competing interest statement

MIT has obtained patents for some of the ligands that are described in this Communication from which S.L.B. and former/current co-workers receive royalty payments.

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