Catalytic asymmetric nucleophilic fluorination using BF3·Et2O as fluorine source and activating reagent

Weiwei Zhu, Xiang Zhen, Jingyuan Wu, Yaping Cheng, Junkai An, Xingyu Ma, Jikun Liu, Yuji Qin, Hao Zhu, Jijun Xue and Xianxing Jiang ()
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Weiwei Zhu: Sun Yat-Sen University
Xiang Zhen: Lanzhou University
Jingyuan Wu: Sun Yat-Sen University
Yaping Cheng: Sun Yat-Sen University
Junkai An: Lanzhou University
Xingyu Ma: Sun Yat-Sen University
Jikun Liu: Lanzhou University
Yuji Qin: Sun Yat-Sen University
Hao Zhu: Lanzhou University
Jijun Xue: Lanzhou University
Xianxing Jiang: Sun Yat-Sen University

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Fluorination using chiral catalytic methods could result in a direct access to asymmetric fluorine chemistry. However, challenges in catalytic asymmetric fluorinations, especially the longstanding stereochemical challenges existed in BF3·Et2O-based fluorinations, have not yet been addressed. Here we report the catalytic asymmetric nucleophilic fluorination using BF3·Et2O as the fluorine reagent in the presence of chiral iodine catalyst. Various chiral fluorinated oxazine products were obtained with good to excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to >20:1 dr). Control experiments (the desired fluoro-oxazines could not be obtained when Py·HF or Et3N·3HF were employed as the fluorine source) indicated that BF3·Et2O acted not only as a fluorine reagent but also as the activating reagent for activation of iodosylbenzene.

Date: 2021
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DOI: 10.1038/s41467-021-24278-3

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