Decarboxylative cross-coupling reactions for P(O)-C bond formation

Abstract

Phosphorus-containing compounds are one of the most important classes of organic compounds, which have wide applications in organic chemistry, medicinal chemistry, agricultural chemistry, and materials chemistry. In particular, organophosphorus compounds bearing a P(O)-C bond have attracted significant attention in recent decades due to their widespread biological and pharmacological activities. In this review, we will highlight the most important developments in the construction of P(O)-C bonds through decarboxylative C-P cross-coupling reactions. The literature has been surveyed from 2011 to May 2018.

Fig. 1. Selected examples of drugs containing a P(O)–C bond.

Fig. 2. C–P cross-coupling routes for the formation of P(O)–C bond.

Scheme 1. Cu-catalyzed decarboxylative coupling reactions of alkenyl acids with P(O)H compounds developed by Hu and co-workers.

Scheme 2. Mechanistic proposal for the formation of alkenylphosphorus compounds 6.

Scheme 3. Ni-catalyzed decarboxylative coupling of alkenyl acids 7 with P(O)–H compounds 8.

Scheme 4. Tang–Wang's synthesis of (E)-1-alkenylphosphorus compounds 12.

Scheme 5. Mechanistic proposal for the reactions in Scheme 4.

Scheme 6. Transition-metal-free phosphorylation of alkenyl acid derivatives with P(O)H compounds reported by Liu.

Scheme 7. Synthesis of estrone derivative 17 through a decarboxylative C–P cross-coupling reaction.

Scheme 8. Mechanism that accounts for the formation of (E)-1-alkenylphosphorus compounds 15.

Scheme 9. Cu/Pd-catalyzed decarboxylative C–P cross-coupling of alkynyl acids 18 with P(O)H compounds 19.

Scheme 10. Mechanism proposed to explain the synthesis of alkynylphosphorus compounds 20.

Scheme 11. Decarboxylative cross-coupling of alkynyl acids 21 with dialkyl H-phosphonates 22 mediated by Cu(OAc)·H₂O.

Scheme 12. Proposed mechanistic pathways for the formation of alkynylphosphorus compounds 23.

Scheme 13. Cu-catalyzed decarboxylative cross-coupling of alkynyl acids 24 with H-phosphine oxides 25 for the stereoselective synthesis of (E)-alkenylphosphine oxides 26.

Scheme 14. Mechanistic explanation of the synthesis of (E)-alkenylphosphine oxide derivatives 26.

Scheme 15. Ag-mediated cascade reaction of arylpropiolic acids 27 with diarylphosphine oxides 28 developed by Gao.

Scheme 16. Mechanistic proposal for the reaction in Scheme 14.

Scheme 17. Pd/Ag-catalyzed decarboxylative C–P coupling of o-nitrobenzoic acids 30 with H-phosphonates 31.

Scheme 18. Plausible mechanism for the formation of aryl phosphonates 32.

Scheme 19. Cu-catalyzed three-component decarboxylative coupling of natural α-amino acids 33 with aromatic aldehydes 34 and P(O)H compounds 35.

Scheme 20. Mechanism that accounts for the formation of tertiary amino phosphorus compounds 36.

Scheme 21. Kaboudin's synthesis of N-benzyl-2-(di(ethyl)phosphoryl)pyrrolidine derivatives 40.

Scheme 22. Oxidative decarboxylative coupling of alkynyl acids 41 with P(O)H compounds 42 developed by Song.

Scheme 23. Mechanistic proposal for the reaction in Scheme 22.

Scheme 24. CuSO₄·5H₂O-catalyzed oxidative decarboxylative coupling of alkynyl acids 44 with H-phosphine oxides 45 into β-ketophosphine oxides 46.

Scheme 25. Plausible mechanism for the formation of β-ketophosphine oxides 46.

Scheme 26. Cu/Fe-catalyzed oxidative decarboxylative coupling of various alkenyl acids 47 with H-phosphonates 48.

Scheme 27. Chen's synthesis of β-keto phosphorus compounds 52.

Scheme 28. Plausible mechanism for the formation of β-keto phosphorus compounds 52.

Akram Hosseinian

Fatemeh Alsadat Hosseini Nasab

Sheida Ahmadi

Zahra Rahmani

Esmail Vessally