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. 2023 Nov;34(18):2169-2174.
doi: 10.1055/a-2108-9895. Epub 2023 Jul 31.

N-Functionalization of 1,2-Azaborines

Hyelee Lee  1   2 , Marisol Alvarado  1 , Sarah Ingram  1   3 , Bo Li  1 , Shih-Yuan Liu  1
Affiliations

N-Functionalization of 1,2-Azaborines

Hyelee Lee et al. Synlett. 2023 Nov.

Abstract

General protocols for the N-functionalization of 1,2-azaborines with C(sp3), C(sp2), or C(sp) electrophiles are described. The syntheses of a new parental BN isostere of trans-stilbene and a BN isostere of a lisdexamfetamine derivative were accomplished with the developed methodology.

Keywords: BN heterocycles; N-functionalization; amination; azaborines; cross-coupling.

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Conflict of interest statement

Conflict of Interest The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1
Late-stage functionalization of 1,2-azaborines
Scheme 2
Scheme 2
Synthesis of the BN isostere of trans-stilbene
Scheme 3
Scheme 3
Synthesis of a BN-lisdexamfetamine analogue
See this image and copyright information in PMC

References

    1. Liu Z; Marder TB Angew. Chem. Int. Ed 2008, 47, 242. - PubMed
    2. Bosdet MJD; Piers WE Can. J. Chem 2009, 87, 8.
    3. Campbell PG; Marwitz AJV; Liu S-Y Angew. Chem. Int. Ed 2012, 51, 6074. - PMC - PubMed
    4. Giustra ZX; Liu S-YJ Am. Chem. Soc 2018, 140, 1184. - PMC - PubMed
    1. McConnell CR; Liu S-Y Chem. Soc. Rev 2019, 48, 3436. - PMC - PubMed
    1. Marwitz AJV; Abbey ER; Jenkins JT; Zakharov LN; Liu S-Y Org. Lett 2007, 9, 4905. - PubMed
    2. Lamm AN; Garner EB; Dixon DA; Liu S-Y Angew. Chem. Int. Ed 2011, 50, 8157. - PMC - PubMed
    3. Rudebusch GE; Zakharov LN; Liu S-Y Angew. Chem. Int. Ed 2013, 52, 9316. - PMC - PubMed
    4. Brown AN; Zakharov LN; Mikulas T; Dixon DA; Liu S-Y Org. Lett 2014, 16, 3340. - PMC - PubMed
    1. Pan J; Kampf JW; Ashe AJ III. Org. Lett 2007, 9, 679. - PubMed
    1. Brown AN; Li B; Liu S-YJ Am. Chem. Soc 2015, 137, 8932. - PMC - PubMed
    2. Brown AN; Li B; Liu S-Y Tetrahedron 2019, 75, 580. - PMC - PubMed

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