Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes: Synthesis and applications

Thies Thiemann, Kuniharu Umeno, Jian Wang, Yumiko Tabuchi, Kazuya Arima, Masataka Watanabe, Yasuko Tanaka, Hideki Gorohmaru, Shuntaro Mataka

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(0) mediated C–C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4–9. Suzuki–Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4–9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C–C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.

Original languageEnglish
Pages (from-to)2090-2110
Number of pages21
JournalJournal of the Chemical Society. Perkin Transactions 1
Volume2
Issue number18
DOIs
Publication statusPublished - Mar 18 2002
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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