Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by CC Bond Cleavage
A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides wer...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 43; p. 12692 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley Subscription Services, Inc
19.10.2015
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| Edition | International ed. in English |
| Online Access | Get full text |
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| Abstract | A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides were also readily prepared. Preliminary mechanistic studies reveal that the reaction likely proceeds by a radical-mediated CC bond cleavage/CN3 bond formation pathway. |
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| AbstractList | A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides were also readily prepared. Preliminary mechanistic studies reveal that the reaction likely proceeds by a radical-mediated CC bond cleavage/CN3 bond formation pathway. |
| Author | Zhao, Huijun Huan, Leitao Zhu, Chen Ren, Rongguo |
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| Copyright | 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| DOI | 10.1002/anie.201506578 |
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| Snippet | A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in... |
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| Title | Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by CC Bond Cleavage |
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