期刊
NATURE CATALYSIS
卷 3, 期 9, 页码 710-718出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/s41929-020-0487-0
关键词
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资金
- JST ERATO [JPMJER1302]
- JSPS KAKENHI [19H05463, JP17H04868, JP19H02700, JP19H02701, JP19K22183]
- Shorai Foundation for Science and Technology
- Noguchi Institute
- World Premier International Research Center Initiative (WPI), Japan
The discoveries of new forms of carbon have always opened doors to new science and technology. In 1991, three-dimensional (3D) periodic carbon crystals with negative Gaussian curvatures that consist of six- and eight-membered rings were proposed. To realize these 3D periodic carbon crystals (known as Mackay crystals), methods for creating polyaromatic structures embedding eight-membered rings must be developed. Here we report two annulative coupling reactions that form an eight-membered ring through catalytic C-H functionalization. We have discovered thatbay-chlorinated polyaromatics undergo either annulative dimerization or cross-coupling with biphenylene in the presence of a palladium catalyst to form various hitherto inaccessible polyaromatics embedding an eight-membered ring. The threefold annulative cross-coupling of 1,5,9-trichlorotriphenylene allowed construction of a highly curved nanocarbon. The present work not only demonstrates the potential of annulative coupling for constructing octagonal nanocarbons but also provides a conceptual pathway for the synthetic realization of 3D periodic carbon crystals. The Mackay crystal is a proposed-but synthetically unachieved-nanocarbon molecule that is anticipated to have many desirable properties. Now, a strategy based on annulative coupling of chlorophenanthrene derivatives is reported, allowing streamlined access to an important substructure.
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