- Bronsted acid mediated nitrogenation of propargylic alcohols: An efficient approach to alkenyl nitriles
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A novel and efficient approach to alkenyl nitriles from readily available propargylic alcohols has been developed. This nitrogenation reaction is transition-metal-free and could be conducted under air at ambient temperature, which makes this protocol promising and practical. Moreover, NH4Br is disclosed as an efficient additive to promote the stereoselectivity of this reaction. the Partner Organisations 2014.
- Huang, Xiaoqiang,Jiao, Ning
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supporting information
p. 4324 - 4328
(2014/06/23)
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- Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
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An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol %) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process.
- Jereb, Marjan
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experimental part
p. 3861 - 3867
(2012/06/30)
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- Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf
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Highly useful carbon-carbon bond forming reactions using stable allenyl, propargyl, or allyl-propargyl hybrid cations have been developed. These carbocations could be generated from silyl 1-(π-donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 °C to room temperature and could be attacked nucleophilically by electron rich arenes, allylsilanes, or enol silyl ethers, giving rise to allenes, alkynes, and their derivatives. A novel method for regio- and stereoselective synthesis of conjugated enynes utilizing allyl-propargyl hybrid cations has also been established.
- Ishikawa,Okano,Aikawa,Saito
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p. 4635 - 4642
(2007/10/03)
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