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. 2020 Feb 10;59(7):2745-2749.
doi: 10.1002/anie.201913388. Epub 2020 Jan 16.

Aminoazanium of DABCO: An Amination Reagent for Alkyl and Aryl Pinacol Boronates

Xingxing Liu  1   2 , Qing Zhu  2   3 , Du Chen  2   3 , Lu Wang  2 , Liqun Jin  1 , Chao Liu  2   4
Affiliations

Aminoazanium of DABCO: An Amination Reagent for Alkyl and Aryl Pinacol Boronates

Xingxing Liu et al. Angew Chem Int Ed Engl. .

Abstract

The aminoazanium of DABCO (H2 N-DABCO) has been developed as a general and practical amination reagent for the direct amination of alkyl and aryl pinacol boronates. This compound is stable and practical for use as a reagent. Various primary, secondary. and tertiary alkyl-Bpin and aryl-Bpin substrates were aminated to give the corresponding amine derivatives. The amination is stereospecific. The anti-Markovnikov hydroamination of olefins was easily achieved by catalytic hydroboration with HBpin and in subsequent situ amination using H2 N-DABCO. Moreover, the combination of 1,2-diboration of olefins, using B2 pin2 , with this amination process achieved the unprecedented 1,2-diamination of olefins. The amination protocol was also successfully extended to aryl pinacol boronates.

Keywords: amination; amines; arenes; boron; synthetic methods.

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References

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