Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 16, Pages 10967-10981Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01238
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Funding
- NSFC [21872028]
- Natural Science Foundation of Fujian Province [2020J01149]
- Fujian Province University Fund for New Century Excellent Talents
- College Students Innovation and Entrepreneurship Training Program [CXXL-2022224, CXXL2022234]
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Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials has been achieved. Mn(OAc)3.2H2O selectively promotes different reactions leading to the formation of two distinct products.
Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3.2H2O selectively promoted an intramolecular radical C-H/C-H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while an intramolecular radical C-H/N-H dehydrogenative coupling reaction could proceed via electrochemistry to deliver isoindolo[2,1-a]indoles. Plausible mechanisms of the chemodivergent reactions were proposed.
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