- Rhodium Complex-Catalyzed Desilylative Cyclocarbonylation of 1-Aryl-2-(trimethylsilyl)acetylenes: A New Route to 2,3-Dihydro-1H-inden-1-ones
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Under water gas shift reaction conditions, 1-aryl-2-(trimethylsilyl)acetylenes undergo Rh-catalyzed desilylative cyclocarbonylation to give 2,3-dihydro-1H-inden-1-ones and trimethylsilanol.A wide variety of functional groups, such as methoxy, chloro, acetyl, ethoxycarbonyl, cyano, and trifluoromethyl, are tolerated on the aromatic ring under the reaction conditions.The products were obtained in good to excellent yield whether the substituent on the aromatic ring was electron-donating or electron-withdrawing.The cyclizations of substrates bearing a meta substituent onthe aromatic ring regiospecifically gave 5-substituted-2,3-dihydro-1H-inden-1-ones except when the meta substituent was a methoxy group.The desilylative cyclocarbonylation is an alternative to the conventional preparation of 2,3-dihydro-1H-inden-1-ones, an intramolecular Friedel-Crafts acylation.A possible mechanism for the process is described.
- Takeuchi, Ryo,Yasue, Hiroyuki
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p. 5386 - 5392
(2007/10/02)
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- The Stereochemistry of Organometallic Compounds. XXXIV. Regioselection in the Hydroformylation of Silylalkenes
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The regiochemistry of hydroformylation of alkenes can be controlled by use of bulky silyl groups attached to the alkene.Use of the t-butyldiphenylsilyl group leads to almost total regiocontrol and the method has been applied to the synthesis of aldols.
- Doyle, M. Michael,Jackson, W. Roy,Perlmutter, Patrick
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p. 1907 - 1918
(2007/10/02)
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