Pd-P(t-Bu)3-catalyzed consecutive cross-coupling of p-phenylenedizinc compound with two different electrophiles leading to unsymmetrically 1,4-disubstituted benzenes

Takahiro Kawamoto, Shogo Ejiri, Kana Kobayashi, Shunsuke Odo, Yasushi Nishihara, Kentaro Takagi

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Abstract

(Chemical Equation Presented) Pd-P(t-Bu)3 was found to be a chemoselective catalyst for the reaction of p-phenylenedizinc compound with equimolar amounts of carbon electrophiles to afford the single cross-coupling products in good yields, effectively suppressing the formation of double cross-coupling products. The subsequent additions of other electrophiles to the resulting solutions caused the second cross-coupling of the incipient products to take place, achieving a novel and efficient one-pot synthesis of unsymmetrically 1,4-disubstituted benzenes. The origin of the observed high chemoselectivity was speculated.

Original languageEnglish
Pages (from-to)1601-1604
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number4
DOIs
Publication statusPublished - Feb 15 2008

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ASJC Scopus subject areas

  • Organic Chemistry

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