期刊
NATURE
卷 574, 期 7779, 页码 516-+出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/s41586-019-1655-8
关键词
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资金
- National Basic Research Program of China [973-2015CB856600]
- National Natural Science Foundation of China [21532009, 21821002, 21790330, 21761142010]
- Science and Technology Commission of Shanghai Municipality [17XD1404500, 17QA1405200, 17JC1401200]
- Strategic Priority Research Program [XDB20000000]
- Key Research Program of Frontier Science [QYZDJSSW-SLH055]
- Youth Innovation Promotion Association of the Chinese Academy of Sciences [2018292]
- Research Grants Council of Hong Kong [HKUST 16304416, 16304017]
Methods for selective C-H bond functionalization have provided chemists with versatile and powerful toolboxes for synthesis, such as the late-stage modification of a lead compound without the need for lengthy de novo synthesis(1-5). Cleavage of an sp(3) C-H bond via hydrogen atom transfer (HAT) is particularly useful, given the large number of available HAT acceptors and the diversity of reaction pathways available to the resulting radical intermediate(6-17). Site-selectivity, however, remains a formidable challenge, especially among sp(3) C-H bonds with comparable properties. If the intermediate radical could be further trapped enantioselectively, this should enable highly site- and enantioselective functionalization of C-H bonds. Here we report a copper (Cu)-catalysed site- and enantioselective allylic C-H cyanation of complex alkenes, in which a Cu(ii)-bound nitrogen (N)-centred radical plays the key role in achieving precise site-specific HAT. This method is shown to be effective for a diverse collection of alkene-containing molecules, including sterically demanding structures and complex natural products and pharmaceuticals.
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