Citation: Zhenguo Zhang, Lanyang Li, Xinlong Zong, Yongheng Lv, Shuanglei Liu, Liang Ji, Xuefei Zhao, Zhenhua Jia, Teck-Peng Loh. "Water" accelerated B(C₆F₅)₃-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model[J]. Chinese Chemical Letters, ;2025, 36(7): 110504. doi: 10.1016/j.cclet.2024.110504 shu

"Water" accelerated B(C₆F₅)₃-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model

Zhenguo Zhang ^{a, b, c} ,
Lanyang Li ^a ,
Xinlong Zong ^a ,
Yongheng Lv ^a ,
Shuanglei Liu ^a ,
Liang Ji ^a ,
Xuefei Zhao ^{a, *,} ,
Zhenhua Jia ^{a, b, c, *,} ,
Teck-Peng Loh ^{a, b, c, *,}

a.
School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
b.
College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China
c.
School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

xfzhao@njtech.edu.cn

iaszhjia@njtech.edu.cn

teckpeng@ntu.edu.sg

Received Date: 12 June 2024
Revised Date: 15 September 2024
Accepted Date: 24 September 2024
Available Online: 26 September 2024

Figures(5)

A "water" accelerated metal-free catalytic system has been discovered for the Mukaiyama-aldol reaction. The system involves the use of B(C₆F₅)₃ as a catalyst, which is water-tolerant and able to activate the carbonyl group through a hydrogen bonding network generated by the catalyst. This activation method allows the reactions to be performed with very low catalyst loading, as low as 0.5 mol%. The scope of substrates is broad and a wide variety of functional groups are well tolerated. Diverse aliphatic aldehydes, aromatic aldehydes, unsaturated aldehydes and aromatic ketones coupled with silyl enol ethers/silyl ketone acetals to generate their corresponding β–hydroxy carbonyl compounds in moderate to good yields. This discovery represents a significant advancement in the field of organic synthesis, as it provides a new, practical and sustainable solution for carbon-carbon bond formation in water.
- B(C₆F₅)₃-catalysis,
- Hydrogen bonding network,
- Water-acceleration,
- Mukaiyama-aldol reaction,
- Outer-sphere activation model
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"Water" accelerated B(C6F5)3-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model

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通讯作者: 陈斌, bchen63@163.com

"Water" accelerated B(C₆F₅)₃-catalyzed Mukaiyama-aldol reaction: Outer-sphere activation model