Rh-catalyzed Negishi alkyl-aryl cross-coupling leading to α- or β-phosphoryl-substituted alkylarenes

Hideki Takahashi, Shinya Inagaki, Naoko Yoshii, Fuxing Gao, Yasushi Nishihara, Kentaro Takagi

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23 Citations (Scopus)

Abstract

The catalytic cross-coupling between ArZnX and ICH2(CH 2)nP(O)(OEt)2 (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, β-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.

Original languageEnglish
Pages (from-to)2794-2797
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number7
DOIs
Publication statusPublished - Apr 3 2009

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ASJC Scopus subject areas

  • Organic Chemistry

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