Radical Cascade Cyclization Involving C(sp3)—H Functionalization of Unactivated Cycloalkanes

doi:10.6023/cjoc202208001

Abstract

Unactivated cycloalkane is one of the most extensive natural resources, and it is of great significance to develop mild and efficient strategies to achieve C(sp³)—H of unactivated cycloalkanes. At the same time, the preparation of ring compounds is one of the hotspots in organic synthesis and medicinal chemistry. Because of the advantages of mild conditions and high reactivity, radical cascade cyclization involving C(sp³)—H functionalization of unactivated cycloalkanes can simultaneously meet the above requirements and synthesize cyclic molecules with potential applications in high atomic- and step- economy manner. In this review, from the point of view of iron catalysis, copper catalysis, and metal-catalyst-free systems, the advances in radical cascade cyclization involving C(sp³)—H functionalization of unactivated cycloalkanes in recent ten years are summarized.

Key words: unactivated cycloalkane, C(sp³)—H functionalization, radical cascade cyclization, catalytic system

Cite this article

Rongnan Yi, Jiaozhe Li, Dongkai Wang, Wenting Wei. Radical Cascade Cyclization Involving C(sp³)—H Functionalization of Unactivated Cycloalkanes[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4111-4121.

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Fig. & Tab. 22

Scheme 1. Radical cascade bi-cyclization of 1,7-enynes with simple cycloalkanes

Scheme 2. Radical cascade bi-cyclization of O-tethered 1,7- enynes with simple cycloalkanes

Scheme 3. Radical cascade cyclization of acrylamides with simple cycloalkanes

Scheme 4. Alkylarylation of acrylamides with simple alkanes

Scheme 5. Radical cascade cyclization of isocyanides with simple cycloalkanes

Scheme 6. Radical cascade cyclization of N-allyl anilines with simple cycloalkanes

Scheme 7. Radical cascade cyclization of activated alkynes with unactivated cycloalkanes

Scheme 8. Radical cascade cyclization of diaryl(arylethynyl)- phosphine oxides with unactivated cycloalkanes

Scheme 9. Alkylation/denitrative dearomatization of nitrobiarylalkynones with cycloalkanes

Scheme 10. Radical cascade cyclization of pyridines with simple alkanes

Scheme 11. Radical cascade cyclization of olefinic amides with simple alkanes

Scheme 12. Oxidative cyclization of vinyl azides with cycloalkanes

Scheme 13. Radical cascade cyclization of aryl isocyanates/ isothiocyanates with simple alkanes

Scheme 14. Radical cascade cyclization of N-phenyl-cinnam- amides with simple alkanes

Scheme 15. Radical cascade cyclization of N-allylbenzamides with cycloalkanes

Scheme 16. Radical cascade cyclization of 2-cyano-3-arylani- line derived acrylamides with simple cycloalkanes

Scheme 17. Radical cascade cyclization of 2-arylbenzoimidazoles with unactivated cycloalkanes

Scheme 18. Radical cascade cyclization of biaryl vinyl ethers with unactivated alkanes

Scheme 19. Radical cascade cyclization of alkene substituted quinazolinones with unactivated alkanes

Scheme 20. Radical cascade cyclization of vinyl isocyanides with unactivated alkanes

Scheme 21. Radical cascade cyclization of isonitriles with cycloalkanes

Scheme 22. Carboannulation of ynones with alkanes

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涉及未活化环烷烃C(sp³)—H官能化的自由基串联环化反应

Radical Cascade Cyclization Involving C(sp³)—H Functionalization of Unactivated Cycloalkanes

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Fig. & Tab. 22

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涉及未活化环烷烃C(sp3)—H官能化的自由基串联环化反应