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Published January 5, 2018 | Supplemental Material
Journal Article Open

Isocanthine Synthesis via Rh(III)-Catalyzed Intramolecular C-H Functionalization


An efficient synthesis of substituted isocanthines has been achieved using an intramolecular Rh(III)-catalyzed C–H functionalization of alkyne-tethered indoles in the presence of catalytic tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate and stoichiometric copper(II) acetate. This isocanthine synthesis tolerates a variety of electronically diverse 5- or 6-substituted indoles with N-tethered alkyne coupling partners and can also be extended to pyrrole derivatives for the synthesis of annulated 5-azaindoles.

Additional Information

© 2017 American Chemical Society. Received: October 27, 2017; Published: November 28, 2017. This paper is dedicated to Professor Richard C. Larock, Emeritus Professor of Chemistry at Iowa State University on the occasion of his 73rd birthday. The authors would like to thank Dr. Kevin Kou (University of California, Berkeley) for helpful discussion, Dr. Kenji Kurita (Genentech, Inc.) for collecting HRMS data, Mr. Malcolm Huestis (Genentech, Inc.) for providing catalyst C1, and Dr. Francis Gosselin (Genentech, Inc.) for proof-reading the manuscript. AYC, RS and BMS are grateful to the NSF under the CCI Center for Selective C–H Functionalization (CHE-1205646 and CHE-1700982) for support. Part of this research was presented in the Symposium of Applications of C–H Functionalization, Pacifichem, Honolulu, HI in December, 2015. AYC was an undergraduate summer intern at Genentech, Inc. where this work was initiated. The authors declare no competing financial interest.

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Supplemental Material - jo7b02731_si_001.pdf

Supplemental Material - jo7b02731_si_002.pdf

Supplemental Material - jo7b02731_si_003.cif


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