Citation: Kun Wang, Tianxue Gong, Yaohuang Huang, Boyang Han, Hanxiao Yang, Pavlo O. Dral, Weiwei Fang. Bornylimidazo[1,5–a]pyridin-3-ylidene allylic Pd catalyst with optimal electronic and steric properties for synthesis of 3,3′-disubstituted oxindoles[J]. Chinese Chemical Letters, ;2025, 36(7): 110539. doi: 10.1016/j.cclet.2024.110539 shu

Bornylimidazo[1,5–a]pyridin-3-ylidene allylic Pd catalyst with optimal electronic and steric properties for synthesis of 3,3′-disubstituted oxindoles

Kun Wang ^{a, 1} ,
Tianxue Gong ^{a, 1} ,
Yaohuang Huang ^b ,
Boyang Han ^a ,
Hanxiao Yang ^a ,
Pavlo O. Dral ^{b, *,} ,
Weiwei Fang ^{a, *,}

a.
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
b.
State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry, Xiamen University, Xiamen 361005, China

dral@xmu.edu.cn

wwfang2020@njfu.edu.cn

Received Date: 22 April 2024
Revised Date: 18 September 2024
Accepted Date: 9 October 2024
Available Online: 10 October 2024

Figures(6)

A robust bulky bornylimidazo[1,5–a]pyridin-3-ylidene allylic Pd complex was synthesized and well characterized. DFT calculations indicated that the ligand acts as a strong σ-donor and π-acceptor endowing the active Pd(0) center with high electron density and good coordination towards olefin. The introduction of a bulky, rigid bornyl ring further improved the catalytic efficacy due to the matched steric effects. This catalyst showed high efficiency and versatility in the α-arylation and Heck cyclization/Suzuki cross-coupling reactions at mild reaction conditions. Desired 3,3′-disubstituted oxindoles, especially featuring an allylic-derived C3-quaternary stereocenter were obtained in high yields. Furthermore, the concise synthesis of bioactive heterocycle-fused indoline alkaloids was successfully proved.
- Pd catalyst,
- Cross-coupling reaction,
- DFT calculations,
- 3,3′-Disubstituted oxindoles,
- Imidazo[1,5–a]pyridin-3-ylidene
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