Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 18, Pages 4380-4389Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100555
Keywords
Rhodium; Indole; Alkyne; C-H activation; [4+1] annulation; C-1 synthon
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Funding
- Natural Science Foundation of Zhejiang Province [LY21B020003, LQ19B020003]
- Natural Science Foundation of Ningxia Province [2021AAC03389]
- 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 Funding [2081915037]
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This study achieved the synthesis of functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones by utilizing electron-deficient alkynes as unconventional C-1 synthons in a redox-neutral rhodium(III)-catalyzed [4+1] annulation. The process exhibited high chemo- and regioselectivity, broad substrate scope, good tolerance of functional groups, moderate to high yields, and mild redox-neutral conditions, providing a robust method to access valuable 1H-imidazo[1,5-a]indol-3(2H)-ones.
Alkynes generally serve as C-2 synthons in transition-metal-catalyzed C-H annulations, herein, exploiting electron-deficient alkynes as unconventional C-1 synthons, the chemo- and regiospecific synthesis of functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a redox-neutral rhodium(III)-catalyzed [4+1] annulation of N-carbamoyl indoles has been achieved. This process is characterized by high chemo- and regioselectivity, broad substrate scope, good tolerance of functional groups, moderate to high yields and mild redox-neutral conditions, thus affording a robust approach to access valuable 1H-imidazo[1,5-a]indol-3(2H)-ones.
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