Issue 18, 2002

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

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.

Graphical abstract: Elongated phosphoranes by C–C coupling of haloaroylmethylidenetriphenylphosphoranes: synthesis and applications

Supplementary files

Article information

Article type
Paper
Submitted
18 Mar 2002
Accepted
30 Jul 2002
First published
23 Aug 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2090-2110

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

T. Thiemann, K. Umeno, J. Wang, Y. Tabuchi, K. Arima, M. Watanabe, Y. Tanaka, H. Gorohmaru and S. Mataka, J. Chem. Soc., Perkin Trans. 1, 2002, 2090 DOI: 10.1039/B202745N

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