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Issue 21, 2018
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Cascade double isocyanide insertion and C–N coupling of 2-iodo-2′-isocyano-1,1′-biphenyls

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Abstract

A palladium-catalyzed double isocyanide insertion using 2-iodo-2′-isocyano-1,1′-biphenyls followed by copper-catalyzed intramolecular C–N coupling, delivering a unique heterocyclic structure containing both phenanthridine and carbazole scaffolds, has been developed. In this cascade process, four chemical bonds, including two C–C, one C–O, and one C–N bonds are formed consecutively without isolating an intermediate. The strategy of using a functionalized isocyanide in double insertion provides a quick approach for constructing heterocyclic systems with high bond-forming efficiency.

Graphical abstract: Cascade double isocyanide insertion and C–N coupling of 2-iodo-2′-isocyano-1,1′-biphenyls

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Publication details

The article was received on 24 Apr 2018, accepted on 02 May 2018 and first published on 02 May 2018


Article type: Communication
DOI: 10.1039/C8OB00956B
Citation: Org. Biomol. Chem., 2018,16, 3893-3896

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    Cascade double isocyanide insertion and C–N coupling of 2-iodo-2′-isocyano-1,1′-biphenyls

    H. Sun, S. Tang, D. Li, Y. Zhou, J. Huang and Q. Zhu, Org. Biomol. Chem., 2018, 16, 3893
    DOI: 10.1039/C8OB00956B

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