Recent Advances in Nitrene/Alkyne Metathesis Cascade Reaction

doi:10.6023/cjoc202109035

Abstract

Catalytic nitrene transformations to N-containing molecules through direct C—N bond formation have experienced a dramatic development in the last decades. Although a variety of nitrene precursors have been disclosed under the corresponding catalytic conditions, which play a principal role in the synthesis of nitrogen-containing molecules with structural complexity, the types of nitrene transfer reactions mainly limited to the amination, aziridination, sulfimidation, and few others. In this area, reviews focused on different nitrene precursors, catalytic strategy (or metal catalysts), and challenging synthesis have been well-documented. In this review, the catalytic approaches of nitrene addition with alkynes, mainly nitrene/alkyne metathesis cascade reactions are outlined, which provide expeditious access to polycyclic, fused, and spiro N-heterocycles with structural diversity.

Key words: nitrene, α-imino carbene, N-heterocycle, nitrene/alkyne metathesis, cascade reaction

Cite this article

Kemiao Hong, Jingjing Huang, Minghan Yao, Xinfang Xu. Recent Advances in Nitrene/Alkyne Metathesis Cascade Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 344-352.

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Fig. & Tab. 13

Figure 1. Publication and citation report of nitrene from Web of Science (1967~2021)

Scheme 1. Summary of nitrene precursors and catalysts/catalytic conditions

Scheme 2. Summary of catalytic nitrene transfer reactions

Scheme 3. Rh-catalyzed intramolecular cascade NAM reaction terminated by ylide rearrangement

Scheme 4. Rh-catalyzed intermolecular cascade NAM reaction terminated by ylide rearrangement

Scheme 5. Asymmetric cascade NAM reaction terminated by ylide arrangement

Scheme 6. Cascade NAM reaction terminated by a formal C—N bond insertion

Scheme 7. Cascade NAM reaction terminated by aromatic C—H functionalization or cyclopropanation

Scheme 8. Cascade NAM reaction terminated by Buchner reaction

Scheme 9. Cu-catalyzed cascade NAM reaction terminated by Buchner reaction or oxidation

Scheme 10. Cascade NAM reaction terminated by oxidation

Scheme 11. Cascade NAM reaction terminated by 1,2-alkyl migration

Scheme 12. Fe-catalyzed formal [3+2] annulation via metalloradical intermediate

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