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. 2021 Dec 6;60(50):26327-26331.
doi: 10.1002/anie.202109461. Epub 2021 Nov 10.

Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates

Qiang Wang  1 , Maria Biosca  1 , Fahmi Himo  1 , Kálmán J Szabó  1
Affiliations

Electrophilic Fluorination of Alkenes via Bora-Wagner-Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates

Qiang Wang et al. Angew Chem Int Ed Engl. .

Abstract

The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via bora-Wagner-Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner-Meerwein rearrangement of the presented electrophilic fluorination reactions.

Keywords: DFT modeling; boron; fluorination; organic synthesis; rearrangement.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Reactions occurring with [1.2]‐aryl/alkyl or boron migrations.
Figure 2
Figure 2
Examples for organoboron and difluoromethyl containing bioactive compounds.
Figure 3
Figure 3
Calculated free energy profile (kcal mol−1) for the aryl iodide‐catalyzed fluorination of 1 h with 3 c occurring via bora‐Wagner–Meerwein rearrangement.
See this image and copyright information in PMC

References

    1. None
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