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. 2018 Jan 10;140(1):159-162.
doi: 10.1021/jacs.7b12160. Epub 2017 Dec 22.

Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes

Kaitlyn M Logan  1 , Stephen R Sardini  1 , Sean D White  1 , M Kevin Brown  1
Affiliations

Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes

Kaitlyn M Logan et al. J Am Chem Soc. .

Abstract

A Ni-catalyzed method for arylboration is disclosed. The method allows for highly stereoselective arylboration of unactivated alkenes. The reactions utilize a simple Ni-catalyst and work with a broad range of alkenes and aryl bromides. The products represent useful intermediates for chemical synthesis due to the versatility of the C-B bond. Preliminary mechanistic details of the method are also disclosed.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1
Strategies for Carboboration
Scheme 2
Scheme 2
Evaluation of Various Alkenesa aNMR yield refers to yield determined by 1H NMR analysis of the unpurified reaction mixture with an internal standard. Yield refers to yield of isolated product after silica gel column chromatography and is reported as the average of two or more experiments (0.5 mmol scale). The discrepancy between 1H NMR and yield of isolated product is due to a sometimes tedious separation between desired product and a common byproduct, ArBpin. bReaction run for 48 h at 4 °C. c3.0 equiv of ArBr were used. dNMR yield of the Bpin and yield of isolated alcohol after oxidation; see the Supporting Information (SI) for details.
Scheme 3
Scheme 3
Evaluation of Various Aryl Bromidesa aSee Scheme 2. bIsolated as the corresponding BF3K adduct. c3.0 equiv of ArBr were used. dNMR yield of the Bpin and yield of isolated alcohol after oxidation; see the SI for details.
Scheme 4
Scheme 4
Gram Scale Reaction and Further Functionalization of Products
Scheme 5
Scheme 5
Mechanistic Investigations
See this image and copyright information in PMC

References

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