Radical denitrogenative transformations of polynitrogen heterocycles: Building C-N bonds and beyond

doi:10.1016/S1872-2067(21)63814-7

Abstract

Abstract:

Polynitrogen heterocycles are readily available and have recently arisen as versatile synthons for the formation of various C-C and C-X bonds, and medicinally active nitrogen-containing heterocycles. Several cascade reactions, including annulation, radical cascade, and borylation reactions, have been reported in which polynitrogen heterocycles are applied as arylation reagents. The success of these exceptional reactions illustrates the great synthetic potential of polynitrogen heterocycles, which provides a direct and useful approach to arylation reactions and the synthesis of nitrogen-containing heterocycles. The use of photocatalysts to effectively transfer energy from visible light to non-absorbing compounds has gained increasing attention as this method allows for the mild and efficient generation of radicals in a controlled manner. This approach has thus led to new methods that involve unique bond formation reactions. In addition, the use of free radical intermediates stabilized by transition metal catalysts is a powerful way to construct new chemical bonds. The aim of this review is to highlight the rapidly expanding area of radical-initiated denitrogenative cascade reactions of polynitrogen heterocycles and elaborate on their mechanisms from a new perspective by using photocatalysis and metal-based catalysis.

Key words: Denitrogenation, C-N bond, Cyclization, Polynitrogen heterocycles, Radical

Wen-Chao Yang, Cai-Yun Chen, Jun-Feng Li, Zu-Li Wang. Radical denitrogenative transformations of polynitrogen heterocycles: Building C-N bonds and beyond[J]. Chinese Journal of Catalysis, 2021, 42(11): 1865-1875.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63814-7

https://www.cjcatal.com/EN/Y2021/V42/I11/1865

Figures/Tables 20

Scheme 1. Overview of radical-enabled denitrogenative reactions of polynitrogen heterocycles.

Scheme 2. Overview of the different radicals generated from polynitrogen heterocycles.

Scheme 3. Denitrogenative alkyne insertion in 1,2,3-benzotriazinones for the synthesis of isoquinolones.

Scheme 4. Intramolecular denitrogenative cyclization of 1,2,3,4 benzothiatriazine-1,1-dioxides.

Scheme 5. Radical triazole ring opening synthesis.

Scheme 6. Visible light-promoted functionalization of benzotriazoles.

Scheme 7. Photoinitiated denitrogenative cyclization of benzotriazoles and terminal alkynes.

Scheme 8. Photo-induced denitrogenation and C(sp2)-P bond formation of polynitrogen heterocycles using phosphites.

Scheme 9. Denitrogenative transannulation of pyridotriazoles with amines for the synthesis of imidazo[1,5-a]pyridines.

Scheme 10. Denitrogenative transannulation of pyridotriazoles for the synthesis of indolizines with alkynes.

Scheme 11. Co-catalyzed transannulation of pyridotriazoles with isothiocyanates and xanthate esters.

Scheme 12. Fe-catalyzed transannulation of 1,2,3,4-tetrazoles with alkynes or intramolecular cyclization.

Scheme 13. Fe-catalyzed transannulation of 1,2,3,4-tetrazoles coupled with rearrangement.

Scheme 14. Cu-catalyzed denitrogenative ring-opening of 3-aminoindazoles.

Scheme 15. Denitrogenation of 3-aminoindazoles for the synthesis of pyrimido [1,2-b]-indazoles and aromatic nitrile-derived dithioacetals.

Scheme 16. Denitrogenation of 3-aminoindazoles for the synthesis of 1,2-thiobenzonitriles.

Scheme 17. Denitrogenation of 3-aminoindazoles for the synthesis of diverse nitrile-containing triphenylenes.

Scheme 18. Denitrogenation of 3-aminoindazoles for the synthesis of benzothiophenes and isoquinolines.

Scheme 19. Cascade denitrogenative transannulation of 3-aminoindazoles towards 2,2-disubstituted indanones.

Scheme 20. Denitrogenation of 3-aminoindazoles for the C-H arylation of enamines.

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