N-Radical enabled cyclization of 1,n-enynes

doi:10.1016/S1872-2067(20)63702-0

Abstract

Abstract:

Compared to the widely used carbon-centered radicals, N-radicals have been relatively unexplored owing to the lack of practical and convenient production methods. Over the past few years, benefitting from the resurgence of reliable and controllable radical chemistry, N-radicals have been produced via thermal decomposition, oxidants, metal salts, or electrocatalysis. Therefore, numerous N-radical enabled cyclization of 1,n-enynes methods have been developed, providing a versatile and concise synthetic platform for the preparation of complex cyclic systems and natural products containing elaborate ring frameworks. In this review, we will summarize recent advances in the promising field of radical chemistry focusing on the production methods of N-radicals and their cyclization patterns, associated mechanisms, unmet challenges, and future opportunities.

Key words: 1,n-Enynes, N-Radical, Cyclization, C-N bond

Wen-Ting Wei, Qiang Li, Ming-Zhong Zhang, Wei-Min He. N-Radical enabled cyclization of 1,n-enynes[J]. Chinese Journal of Catalysis, 2021, 42(5): 731-742.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(20)63702-0

https://www.cjcatal.com/EN/Y2021/V42/I5/731

Figures/Tables 50

Scheme 1. Intramolecular radical cascade cyclization of iodo-enyne.

Scheme 2. Overview of N-radical enabled cyclization of 1,n-enynes.

Scheme 3. Generation of NO2 radical and its chemoselectivity addition to 1,n-enynes.

Scheme 4. Cascade nitration/cyclization of 1,7-enynes for the synthesis of pyrrolo[4,3,2-de]quinolinones.

Scheme 5. 18O-Labeled experiment and suggested mechanism for cascade nitration/cyclization of 1,7-enynes.

Scheme 6. Nitrative cyclization of 1-ethynyl-2-(vinyloxy)benzenes.

Scheme 7. 18O-Labeled experiments and suggested mechanism for nitrative cyclization of 1-ethynyl-2-(vinyloxy)benzenes.

Scheme 8. Nitro-carbocyclization of 1,6-enynes.

Scheme 9. Suggested mechanism for nitro-carbocyclization of 1,6-enynes.

Scheme 10. Regioselective nitrative cyclization of 1,6-enynes.

Scheme 11. Control experiments and suggested mechanism for regioselective nitrative cyclization of 1,6-enynes.

Scheme 12. Cu(NO3)2/oxone-mediated nitration cyclization of 1,6-enynes.

Scheme 13. Generation of N3 radical and azidation of 1,n-enynes.

Scheme 14. Copper catalyzed [2+2+1] annulation of 1,n-enynes.

Scheme 15. Suggested mechanism for copper catalyzed [2+2+1] annulation of 1,n-enynes.

Scheme 16. Transition-metal controlled diastereodivergent azidation of 1,7-enynes.

Scheme 17. Suggested model for Mn- and Cu-controlled diastereodivergence.

Scheme 18. Azidation/cyclization of 1,6-enynes with N3 sources.

Scheme 19. Control experiments and suggested mechanism for azidation/cyclization of 1,6-enynes with N3 sources.

Scheme 20. Haloazidation of 1,7-enynes for the construction of 3,4-dihydroquinolin-2(1H)ones.

Scheme 21. Suggested mechanism for haloazidation of 1,7-enynes.

Scheme 22. Haloazidation of 1,6-enynes for the synthesis of 2-pyrrolidinones.

Scheme 23. Iodoazidation of para-quinone methides.

Scheme 24. Haloazidation of 1,6-enynes for the synthesis of succinimide derivatives.

Scheme 25. Electrochemical dehydrogenative cyclization of arylamine-tethered 1,5-enynes.

Scheme 26. Suggested mechanism for electrochemical dehydrogenative cyclization of arylamine-tethered 1,5-enynes.

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