Convenient and scalable synthesis of aryldichlorophosphines and primary arylphosphines via perthiophosphonic anhydrides
Date
09/01/2023Metadata
Show full item recordAbstract
A scalable synthetic route to both primary arylphosphines ArPH2 and aryldichlorophosphines ArPCl2 is reported. The C-P bond formation was performed in a highly regiospecific manner through electrophilic substitution of selected aromatic hydrocarbons (ArH) with phosphorus pentasulfide. The resultant perthiophosphonic anhydrides Ar2P2S4 were then reacted with LiAlH4 to give primary phosphines ArPH2. Subsequent reaction of ArPH2 with phosgene solution gives dichlorophosphines ArPCl2. Each reaction step requires minimum purification and uses commercially available and economical precursors. The scope of the reaction was shown to include alkoxy and phenoxy substituted benzenes as well as naphthalene and fluorene as starting materials.
Citation
Picthall , D , Surgenor , B & Kilian , P 2023 , ' Convenient and scalable synthesis of aryldichlorophosphines and primary arylphosphines via perthiophosphonic anhydrides ' , Synthesis , vol. eFirst , pp. A-H . https://doi.org/10.1055/a-1994-2301
Publication
Synthesis
Status
Peer reviewed
ISSN
0039-7881Type
Journal article
Rights
Copyright © 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution and reproduction, so long as the original work is properly cited (https://creativecommons.org/licenses/by/4.0/).
Description
Funding: The authors acknowledge EastChem School of Chemistry for funding.Collections
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