C−C Bond‐Forming Strategy by Manganese‐Catalyzed Oxidative Ring‐Opening Cyanation and Ethynylation of Cyclobutanol Derivatives |
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| Authors: | Rongguo Ren Zhen Wu Yan Xu Prof?Dr Chen Zhu |
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| Institution: | 1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu, China;2. Key Laboratory of Synthesis Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai, China |
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| Abstract: | A novel C?C bond‐forming strategy employing manganese‐catalyzed ring‐opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the γ‐position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring‐opening of cyclobutanol substrates by C?C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical‐mediated C?S bond cleavage. |
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| Keywords: | alkynylation cyanation cyclobutanol manganese catalysis ring-opening |
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