Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 15, Pages 10591-10607Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01256
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Funding
- Natural Science Foundation of Zhejiang Province [LY21B020003]
- National Natural Science Foundation of China [21602022]
- Chengdu Talents Program
- 1000 Talents Program of Sichuan Province
- Longquanyi District Talents Program
- Science and Technology Program of Sichuan Province [2018JY0345]
- Jinhua Branch of Sichuan Industrial Institute of Antibiotics [1003]
- Chengdu University New Faculty Start-up Fund [2081915037]
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This method utilizes internal alkenes embedded with an oxidizing function/leaving group as a rare onecarbon unit for a redox-neutral rhodium(III)-catalyzed chemo- and regiospecific [4+1] annulation, leading to the synthesis of functionalized imidazo[1,5-a]indoles with excellent chemo- and regioselectivity.
Exploiting internal alkenes embedded with an oxidizing function/leaving group as a rare and unconventional onecarbon unit, a redox-neutral rhodium(III)-catalyzed chemo- and regiospecific [4+1] annulation between indoles and alkenes for the synthesis of functionalized imidazo[1,5-a]indoles has been achieved. Internal alkenes employed here can fulfill an unusual [4+1] annulation rather than normal [4+2] annulation/C-H alkenylation. This method is characterized by excellent chemo- and regioselectivity, broad substrate scope, good functional group tolerance, good to high yields, and redox-neutral conditions.
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