Journal
ORGANIC LETTERS
Volume 23, Issue 23, Pages 9184-9188Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03491
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Funding
- National Natural Science Foundation of China [21602089, 21971200]
- Young Key Teacher Foundation of Henan Province [2020GGJS227]
- Natural Science Foundation of Hubei Province [2020CFB642]
- Science and Technology Program of Shenzhen [JCYJ20190809180001759]
- Scientific Research Plan of the Hubei Provincial Department of Education [Q20202002]
- Fundamental Research Funds for the Central Universities [2020kfyXJJS044]
- 100 Talents Program of the Hubei Provincial Government
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A novel palladium-catalyzed direct o-C-H iodination of benzaldehydes was successfully developed using a commercially available 2,5-bis(trifluoromethyl)aniline as the optimal Monodentate Transient Directing Group (MonoTDG), achieving moderate to excellent yields and good selectivity. Importantly, a concise two-step total synthesis of the natural product hernandial was demonstrated by merging this new MonoTDG-assisted C-H iodination with subsequent copper-catalyzed cross-coupling.
The first palladium-catalyzed direct o-C-H iodination of benzaldehydes was successfully developed with the assistance of commercially available 2,5-bis(trifluoromethyl)aniline as the optimal monodentate transient directing group (MonoTDG). Moderate to excellent yields and good selectivity were achieved for a broad substrate scope under mild conditions. More importantly, the synthetic application was demonstrated by a concise two-step total synthesis of the natural product hernandial, which was accomplished by merging this new MonoTDG-assisted C-H iodination and subsequent copper-catalyzed cross-coupling.
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