α-Difluoromethylation on sp<sup>3</sup> Carbon of Nitriles Using Fluoroform and Ruppert–Prakash Reagent
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- Kohsuke Aikawa
- Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan
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- Kenichi Maruyama
- Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan
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- Kazuya Honda
- Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan
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- Koichi Mikami
- Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan
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説明
Difluoromethylation on sp(3) carbon of various nitrile compounds with lithium base and fluoroform (CF3H), which is an ideal difluoromethylating reagent, is shown to provide the α-difluoromethylated nitrile products with an all-carbon quaternary center in moderate to high yields. The Ruppert-Prakash reagent (CF3TMS) is also applicable to the reaction, affording the α-siladifluoromethylated nitrile products, which can be utilized for sequential carbon-carbon bond-forming reactions. These reactions using 1.1 equiv of lithium base, 1.5-2.0 equiv of CF3H or CF3TMS, and easily accessible nitrile derivatives are completed in only a few minutes, resulting in the formation of valuable difluoromethylated compounds.
収録刊行物
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- Organic Letters
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Organic Letters 17 (19), 4882-4885, 2015-09-24
American Chemical Society (ACS)
