Highly selective formation of propargyl- and allenyltrichlorosilanes and their regiospecific addition to various types of aldehydes: preparation of both allenic and homopropargylic alcohols |
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| Institution: | 1. Organic Chemistry Section, National Institute of Interdisciplinary Science and Technology (NIIST), CSIR, Thiruvananthapuram 695 019, Kerala, India;2. Department of Chemistry, University of Kerala, Thiruvananthapuram 695 581, Kerala, India;3. Department of Chemistry, Sree Narayana College, Nattika 680 566, Kerala, India;4. Department of Chemistry, Christian College, Chengannur 689 121, Kerala, India;1. Division of the National Toxicology Program, National Institute of Environmental Health Sciences, 111 T.W. Alexander Drive, PO Box 12233, MD: K2-07, NIH, NTP, Research Triangle Park, NC 27709, United States;2. Battelle Toxicology Northwest, Richland, WA 99352, United States |
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| Abstract: | The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corresponding allenic and homopropargylic alcohols, respectively, in high yields with complete regiospecificity. Remarkably, these carbon–carbon bond-forming reactions simply proceeded in N,N-dimethylformamide (DMF) without using any metal catalysts. |
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