Citation: Nan Li, Xiaoyan Yang, Yanyan Zhu, Fang Wang, Junfang Gong, Maoping Song. Pincer iridium(Ⅲ)-catalyzed enantioselective C(sp³)-H functionalization via carbenoid CH insertion of 3-diazooxindoles with 1, 4-cyclohexadiene[J]. Chinese Chemical Letters, ;2022, 33(5): 2437-2441. doi: 10.1016/j.cclet.2021.11.067 shu

Pincer iridium(Ⅲ)-catalyzed enantioselective C(sp³)-H functionalization via carbenoid CH insertion of 3-diazooxindoles with 1, 4-cyclohexadiene

College of Chemistry, Green Catalysis Center, Zhengzhou University, Zhengzhou 450001, China

gongjf@zzu.edu.cn

mpsong@zzu.edu.cn

Received Date: 23 August 2021
Revised Date: 21 November 2021
Accepted Date: 23 November 2021
Available Online: 27 November 2021

Figures(6)

The asymmetric carbenoid CH insertion of 3-diazooxindoles into 1, 4-cyclohexadiene has been accomplished in the presence of chiral bis(imidazoline) NCN pincer iridium(Ⅲ) complexes as the catalysts. With a catalyst loading of 0.5 mol%, the reactions proceeded smoothly at 0 ℃ to afford a variety of chiral 3-substituted oxindoles in good yields with moderate to excellent enantioselectivities (up to 99% ee). The protocol exhibits good functional group tolerance with respect to 3-diazooxindoles and is readily scaled up to 2 mmol scale without any loss in activity and enantioselectivity. Density functional theory (DFT) calculations have been performed to better understand the reaction mechanism and to explain the stereochemical outcome of the reactions.
- Asymmetric catalysis,
- CH functionalization,
- Pincer iridium(Ⅲ) catalyst,
- Carbenoid CH insertion,
- 3-Diazooxindole,
- Chiral 3-substituted oxindole
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沈阳化工大学材料科学与工程学院沈阳 110142

Pincer iridium(Ⅲ)-catalyzed enantioselective C(sp3)-H functionalization via carbenoid CH insertion of 3-diazooxindoles with 1, 4-cyclohexadiene

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通讯作者: 陈斌, bchen63@163.com

Pincer iridium(Ⅲ)-catalyzed enantioselective C(sp³)-H functionalization via carbenoid CH insertion of 3-diazooxindoles with 1, 4-cyclohexadiene