Journal
ACS CATALYSIS
Volume 10, Issue 21, Pages 12618-12626Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c03808
Keywords
azetidine; dearomatization; diradical species; energy transfer; indolizidine
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Funding
- NSFC [21772219, 21821002, 21801248]
- Science and Technology Commission of Shanghai Municipality [18QA1404900, 18YF1428900]
- Youth Innovation Promotion Association of the Chinese Academy of Sciences [2017302, 2019255]
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Visible-light-induced dearomatization reaction via energy-transfer mechanism is an emerging strategy for the synthesis of highly strained polycyclic molecules. Transient, high-energy diradical species are typically involved in this type of reaction as key intermediates. Herein, we report the visible-light-induced divergent dearomatization of indole-tethered O-methyl oximes, in which the reactions of the open-shelled singlet diradical intermediates toward competitive [2 + 2] cycloaddition or 1,5-hydrogen atom transfer can be achieved with exclusive selectivity. The mechanism has been well supported by a series of experimental and computational investigations. The dearomatization reactions allow the facile synthesis of structurally appealing indoline-fused azetidines and related polycyclic molecules with high efficiency.
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