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Electrophilic Bis-fluorophosphonium Dications: Lewis Acid Catalysts from Diphosphines

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Journal Chem Sci
Specialty Chemistry
Date 2017 Jul 19
PMID 28717457
Citations 7
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Abstract

Stepwise oxidation of 1,8-bis(diphenylphosphino)naphthalene and a series of (oligo)methylene-linked diphosphines with XeF followed by fluoride abstraction yields a family of compounds featuring phosphine, phosphonium and phosphorane moieties in close proximity. The bisphosphonium ions [(CH)(PhPF)] () and [CH(PhPF)] () exhibit remarkable Lewis acidity arising from the proximity of the phosphonium centers. The effectiveness of bisphosphonium dications (, ) is examined in a series of Lewis acid catalysed transformations.

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References
1.
Chiu C, Kim Y, Gabbai F . Lewis acidity enhancement of triarylboranes via peripheral decoration with cationic groups. J Am Chem Soc. 2008; 131(1):60-1. DOI: 10.1021/ja808572t. View

2.
Perez M, Caputo C, Dobrovetsky R, Stephan D . Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis. Proc Natl Acad Sci U S A. 2014; 111(30):10917-21. PMC: 4121813. DOI: 10.1073/pnas.1407484111. View

3.
Kostjuk S, Ganachaud F . Cationic polymerization of vinyl monomers in aqueous media: from monofunctional oligomers to long-lived polymer chains. Acc Chem Res. 2009; 43(3):357-67. DOI: 10.1021/ar900198q. View

4.
Caputo C, Hounjet L, Dobrovetsky R, Stephan D . Lewis acidity of organofluorophosphonium salts: hydrodefluorination by a saturated acceptor. Science. 2013; 341(6152):1374-7. DOI: 10.1126/science.1241764. View

5.
Hudnall T, Kim Y, Bebbington M, Bourissou D, Gabbai F . Fluoride ion chelation by a bidentate phosphonium/borane Lewis acid. J Am Chem Soc. 2008; 130(33):10890-1. DOI: 10.1021/ja804492y. View