Regioselective alkyl transfer from phosphonium ylides to functionalized polyfluoroarenes

Wei Lu, Juan Gao, Jing Kui Yang, Lei Liu, Yuliang Zhao, Hai Chen Wu

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

We report an unprecedented alkyl transfer from phosphonium ylides to polyfluoroarenes in a highly regioselective manner. This reaction allows the introduction of a variety of alkyl groups to the para position of functionalized polyfluoroarenes under mild conditions. The process is found to be compatible with several electrophilic functional groups such as carboxyl, ester, amide and cyano groups. NMR spectroscopy studies and deuterated labeling experiments reveal that the reaction proceeds via an SNAr mechanism and the proton that is transferred to the α-carbon of the alkyl group during the last C-P bond breaking step is from water.

Original languageEnglish (US)
Pages (from-to)1934-1939
Number of pages6
JournalChemical Science
Volume5
Issue number5
DOIs
StatePublished - May 2014

ASJC Scopus subject areas

  • Chemistry(all)

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