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Palladium-Catalyzed Trimerizations of Terminal Arylalkynes: Synthesis of 1,3-Diaryl-2-arylethynyl-1,3-butadienes[1]
Article first published online: 24 JUL 2008
DOI: 10.1002/adsc.200800182
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Wu, Y.-T., Lin, W.-C., Liu, C.-J. and Wu, C.-Y. (2008), Palladium-Catalyzed Trimerizations of Terminal Arylalkynes: Synthesis of 1,3-Diaryl-2-arylethynyl-1,3-butadienes[1]. Adv. Synth. Catal., 350: 1841–1849. doi: 10.1002/adsc.200800182
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 24 JUL 2008
- Manuscript Revised: 4 JUN 2008
- Manuscript Received: 24 MAR 2008
Funded by
- National Science Council of Taiwan. Grant Number: 96-2113-M-006-008-MY2
Keywords:
- alkynes;
- cross-coupling;
- enynes;
- hydroalkynylation;
- palladium
Abstract
Various 1,3-diaryl-2-arylethynyl-1,3-butadienes 7 have been prepared by the Pd-catalyzed trimerization of arylalkynes 4. Their structures and stereochemistry have been confirmed by X-ray crystal analyses. This procedure provides high regioselectivity to generate adducts Z-7 in moderate to excellent yields. The scope, limitations and regioselectivity of this reaction have been investigated. In DMSO at 180 °C, 1,3-di(1-naphthalenyl)-2-(1-naphthalenylethynyl)-1,3-butadiene (7m) underwent 6π-electrocyclization to form 2-(1-naphthalenyl)-3-(1-naphthalenylethynyl)-1,2-dihydrophenanthrene (21). Under acidic conditions, (1Z)-1,3-diphenyl-2-(1-phenylethynyl)-1,3-butadiene (Z-7a) was converted to 1-methyl-3-phenyl-2-(2-phenyl-1-ethionyl)-2-indene (22) in 75% yield.