Recent advances in radical-mediated transformations of 1,3-dienes

doi:10.1016/S1872-2067(21)63919-0

Abstract

Abstract:

1,3-Dienes are a class of easily accessible and versatile feedstock chemicals that can participate in a wide range of reactions to facilitate the synthesis of various valuable allylic compounds. In the past decades, radical methodology has emerged as a powerful tool for organic synthesis by virtue of the fact that diverse highly reactive radical species can usually be generated under mild, neutral and controlled conditions, and allow for rapid generation of molecular complexity. In this review, we critically illustrate the recent advances in the field of radical-mediated transformations of 1,3-dienes based on the different radical precursors and working modes. Wherever possible, particular emphasis is also put on the related mechanistic studies and synthetic applications.

Key words: Radical transformations, 1,3-Dienes, Radical difunctionalization, Transition metal catalysis, Photoredox catalysis

Peng-Zi Wang, Wen-Jing Xiao, Jia-Rong Chen. Recent advances in radical-mediated transformations of 1,3-dienes[J]. Chinese Journal of Catalysis, 2022, 43(3): 548-557.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63919-0

https://www.cjcatal.com/EN/Y2022/V43/I3/548

Figures/Tables 21

Fig. 1. Radical-mediated transformations of 1,3-dienes.

Scheme 1. Cobalt-catalyzed three-component coupling reaction of alkyl halides, 1,3-dienes, and trimethylsilylmethyl magnesium chloride.

Scheme 2. Copper-catalyzed regioselective 1,2-alkylesterification of 1,3-dienes to allylic esters.

Scheme 3. Copper-catalyzed radical-mediated Heck-type alkylation of 1,3-dienes.

Scheme 4. Enantioselective 1,2-difunctionalization of 1,3-butadienes by a Cr/Co bimetallic catalysis system.

Scheme 5. Copper-catalyzed asymmetric diamination of 1,3-dienes.

Scheme 6. Copper-catalyzed 1,2-amino oxygenation of 1,3-dienes with O?acylhydroxylamines and carboxylic acids.

Scheme 7. Intermolecular [3 + 2] cycloadditions of aryl cyclopropyl ketone with 1,3-diene by tandem Lewis acid and photoredox catalysis.

Scheme 8. Dialkylation of 1,3-dienes by dual photoredox and chromium catalysis.

Scheme 9. Photoredox Ni-catalyzed branch-selective reductive coupling between aldehydes with 1,3-dienes.

Scheme 10. Three-component allylation of carbonyls with 1,3-butadiene and alkyl halides via π-allyltitanium complexes.

Scheme 11. Visible-light-driven enantioselective radical carbocyanation of 1,3-dienes via photocatalytic generation of allylcopper complexes.

Scheme 12. Visible-light-induced photoredox-catalyzed decarboxylative alkyl-esterification with 1,3-dienes.

Scheme 13. Photoinduced copper-catalyzed asymmetric radical C-O cross-coupling of 1,3-dienes and ketone oxime esters.

Scheme 14. Photoinduced Pd-catalyzed three-component radical 1,2-aminoalkylation of 1,3-dienes.

Scheme 15. Visible-light-driven photocatalyzed radical amidoarylation of 1,3-butadiene.

Scheme 16. Selective 1,2-aminoisothiocyanation of 1,3-dienes under visible-light-driven photoredox catalysis.

Scheme 17. Photo-sensitized oxy-thiocyanation of 1,3-aryldienes.

Scheme 18. A mild hydroaminoalkylation of 1,3-dienes using a dual cobalt and photoredox catalytic system.

Scheme 19. Visible-light-driven photoredox catalyzed addition of tertiary carbon radicals to electron-deficient 1,3-dienes.

Scheme 20. Visible-light photoredox catalyzed radical 1,4-carbonfunctionlization of 1,3-dienes via π-allylpalladium complexes.

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