Tetrahedron

Dipyrrolidinomethylaminophosphoric acid triamide (DPMPA) as an activator for the samarium diiodide-mediated reduction of alkyl and aryl halides

CE McDonald, JR Ramsey, DG Sampsell, LA Anderson…

Index: McDonald, Chriss E.; Ramsey, Jeremy R.; Sampsell, David G.; Anderson, Laura A.; Krebs, Jordan E.; Smith, Samantha N. Tetrahedron, 2013 , vol. 69, # 14 p. 2947 - 2953

Full Text: HTML

Citation Number: 8

Abstract

The use of the conjugate base of dipyrrolidinomethylaminophosphoric triamide (DPMPA−) as an activator of samarium diiodide is reported. This phosphoramidate has been shown to be a very potent ligand, allowing for the efficient, low-temperature reduction of alkyl and aryl chlorides. Reductive cyclizations of haloalkenylnaphthalenes are also reported.

Related Articles:

A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules

[Kim, Dong Wook; Ahn, Doo-Sik; Oh, Young-Ho; Lee, Sungyul; Kil, Hee Seup; Oh, Seung Jun; Lee, Sang Ju; Kim, Jae Seung; Ryu, Jin Sook; Moon, Dae Hyuk; Chi, Dae Yoon Journal of the American Chemical Society, 2006 , vol. 128, # 50 p. 16394 - 16397]

New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity

[Kim, Dong Wook; Song, Choong Eui; Chi, Dae Yoon Journal of the American Chemical Society, 2002 , vol. 124, # 35 p. 10278 - 10279]

Polymer-supported protic functionalized ionic liquids for nucleophilic substitution reactions: superior catalytic activity compared to other ionic resins

[Shinde, Sandip S.; Lee, Byoung Se; Chi, Dae Yoon Tetrahedron Letters, 2008 , vol. 49, # 27 p. 4245 - 4248]

New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity

[Kim, Dong Wook; Song, Choong Eui; Chi, Dae Yoon Journal of the American Chemical Society, 2002 , vol. 124, # 35 p. 10278 - 10279]

A resin-promoted Williamson's alkyl aryl ether synthesis. Methylation of 2-tert-butyl-5-methylphenol with methyl chloride.

[Kato; Kakamu; Shioiri Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 8 p. 2246 - 2250]

More Articles...