Issue 21, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
24 Apr 2018
Accepted
02 May 2018
First published
02 May 2018

Org. Biomol. Chem., 2018,16, 3893-3896

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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