Aldehyde Addition to 1,3-Butadiyne-Derived Zirconacyclocumulenes: Stereoselective Synthesis of cis-[3]Cumulenols
作者： Xiaoping Fu , Yuanhong Liu , Yuxue Li
DOI: 10.1021/OM100287D
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摘要: The direct addition of aldehydes to zirconacyclocumulenes generated through the coupling reactions benzynezirconocenes with 1,3-butadiynes is achieved cleanly under controlled reaction conditions, which provids a highly stereoselective method for synthesis tetra-substituted [3]cumulenols. DFT calculations suggest that there an equilibrium between seven-membered zirconacyclocumulene (3) and less stable but more reactive five-membered α-alkynylzirconaindene (2) in process. aldehyde reacts zirconaindene intermediate cyclic SE2′ pathway afford cumulenol products after hydrolysis.
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sci-hub.se 参考文章(74)
Titanium and Zirconium in Organic Synthesis Wiley-VCH Verlag GmbH & Co. KGaA. ,(2002) , 10.1002/3527600671
Stéphane Bredeau, Esteban Ortega, Geneviève Delmas, Philippe Richard, Roland Fröhlich, Bruno Donnadieu, Gerald Kehr, Nadine Pirio, Gerhard Erker, Philippe Meunier, Versatile Behavior of Conjugated Diynes with Zirconocene Reactive Species Organometallics. ,vol. 28, pp. 181- 187 ,(2009) , 10.1021/OM800512U
Uwe Rosenthal, Perdita Arndt, Wolfgang Baumann, Vladimir V Burlakov, Anke Spannenberg, Titanocene and zirconocene σ-alkynyl complexes in CC single bond coupling and cleavage reactions Journal of Organometallic Chemistry. ,vol. 670, pp. 84- 96 ,(2003) , 10.1016/S0022-328X(02)02135-6
Ikuo Kinoshita, Masashi Kijima, Hideki Shirakawa, Synthesis of a soluble conjugated cumulene polymer: poly(biphenyl-4,4′-diyl-1,4-bis(4-dodecyloxyphenyl)-buta-1,2,3-triene-1,4-diyl) Macromolecular Rapid Communications. ,vol. 21, pp. 1205- 1208 ,(2000) , 10.1002/1521-3927(20001101)21:17<1205::AID-MARC1205>3.0.CO;2-X
Tamotsu Takahashi, Fu-Yu Tsai, Yanzhong Li, Hui Wang, Yoshihiko Kondo, Masamichi Yamanaka, Kiyohiko Nakajima, Martin Kotora, None, Selective preparation of pyridines, pyridones, and iminopyridines from two different alkynes via azazirconacycles. Journal of the American Chemical Society. ,vol. 124, pp. 5059- 5067 ,(2002) , 10.1021/JA017507+
Uwe Rosenthal, Stable cyclopentynes--made by metals!? Angewandte Chemie. ,vol. 43, pp. 3882- 3887 ,(2004) , 10.1002/ANIE.200401761
Uwe Rosenthal, Paul-Michael Pellny, Frank G. Kirchbauer, Vladimir V. Burlakov, What do titano- and zirconocenes do with diynes and polyynes? Accounts of Chemical Research. ,vol. 33, pp. 119- 129 ,(2000) , 10.1021/AR9900109
Patrick Spies, Gerald Kehr, Roland Fröhlich, Gerhard Erker, Stefan Grimme, Christian Mück-Lichtenfeld, Reaction of Rosenthal's Zirconacyclocumulenes with Chlorophosphines Organometallics. ,vol. 24, pp. 4742- 4746 ,(2005) , 10.1021/OM050336N
Peter Wipf, Heike Jahn, Synthetic applications of organochlorozirconocene complexes Tetrahedron. ,vol. 52, pp. 12853- 12910 ,(1996) , 10.1016/0040-4020(96)00754-5
Chao Chen, Chanjuan Xi, Yuanyuan Liu, Xiaoyin Hong, Generation of benzocyclobutadiene derivatives from zirconaindene derivatives. Journal of Organic Chemistry. ,vol. 71, pp. 5373- 5376 ,(2006) , 10.1021/JO060334S