期刊
TETRAHEDRON
卷 62, 期 49, 页码 11371-11380出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.06.037
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In this article, we describe the development of a general concept for the development of new carbon-carbon bond-forming processes, which is based on Bronsted acid-mediated activation of a siloxy alkyne, followed by efficient interception of the resulting highly reactive ketenium ion by unactivated arenes, alkenes or alkynes. We found that trifluoromethane sulfonimide (HNTf2) proved to be a superior promoter of these reactions compared to a range of other Bronsted acids. This finding could be attributed to a high acidity of HNTf2 in aprotic organic solvents combined with a low nucleophilicity of the NTf2- anion. Depending on the nature of the nucleophile, the carbocyclizations proceeded either via 6-endo-dig or 5-endo-dig manifolds. In the case of 1-sitoxy-1,5-diynes, the cyclizations occurred with a concomitant halide abstraction or arylation. (c) 2006 Elsevier Ltd. All rights reserved.
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