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Issue 23, 2018
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A direct route from white phosphorus and fluorous alkyl and aryl iodides to the corresponding trialkyl- and triarylphosphines

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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

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Publication details

The article was received on 31 Aug 2018, accepted on 16 Oct 2018 and first published on 16 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00943K
Citation: Org. Chem. Front., 2018,5, 3421-3429

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    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

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