Issue 23, 2018

A direct route from white phosphorus and fluorous alkyl and aryl iodides to the corresponding trialkyl- and triarylphosphines

Abstract

Reactions of white phosphorus (P4), fluorous alkyl iodides I(CH2)mRfn (Rfn = CF3(CF2)n−1; 4.0–5.0 equiv./P), and SmI2 (1.0–1.5 equiv./iodide) in THF afford the corresponding trialkylphosphines P((CH2)mRfn)3 (m,n = 2,8; 2,10; 3,6; 3,8; 4,8; 58–92% after workup). Similar reactions with the fluorous aryl iodides IC6H4(3-Rf6), IC6H4(4-Rf6), and IC6H3(3,5-Rf6)2 require the stronger reductants SmBr2 or SmCl2 and give the triarylphosphines P(C6H4(3-Rf6))3, P(C6H4(4-Rf6))3, and P(C6H3(3,5-Rf6)2)3 (23–41%). These transformations involve non-chain radical additions to P4. Advantages versus existing routes to fluorous phosphines, and general strategic issues in the synthesis of organophosphorus compounds, are discussed.

Graphical abstract: A direct route from white phosphorus and fluorous alkyl and aryl iodides to the corresponding trialkyl- and triarylphosphines

Supplementary files

Article information

Article type
Research Article
Submitted
31 Aug 2018
Accepted
16 Oct 2018
First published
16 Oct 2018

Org. Chem. Front., 2018,5, 3421-3429

A direct route from white phosphorus and fluorous alkyl and aryl iodides to the corresponding trialkyl- and triarylphosphines

S. K. Ghosh, C. C. Cummins and J. A. Gladysz, Org. Chem. Front., 2018, 5, 3421 DOI: 10.1039/C8QO00943K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements