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. 2013 Sep 6;15(17):4358-61.
doi: 10.1021/ol401858k. Epub 2013 Aug 19.

Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation

Deepankar Das  1 , Daniel Seidel
Affiliations

Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation

Deepankar Das et al. Org Lett. .

Abstract

Redox-neutral formation of C-P bonds in the α-position of amines was achieved via a process that features a combination of an oxidative α-C-H bond functionalization and a reductive N-alkylation. Benzoic acid functions as an efficient catalyst in this three-component reaction of cyclic secondary amines, aldehydes and phosphine oxides to provide rapid access to α-amino phosphine oxides not easily accessible by classic Kabachnik-Fields reactions.

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Figures

Figure 1
Figure 1
Competing reaction pathways in the α-C–H bond functionalization of amines.
Figure 2
Figure 2
Scope of the three-component reaction.
See this image and copyright information in PMC

References

    1. Kukhar VP, Hudson HR, editors. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Chichester: John Wiley & Sons; 2000.
    1. Lejczak B, Kafarski P. Top. Heterocycl. Chem. 2009;20:31.
    2. Orsini F, Sello G, Sisti M. Curr. Med. Chem. 2010;17:264. - PubMed
    3. Naydenova ED, Todorov PT, Troev KD. Amino Acids. 2010;38:23. - PubMed
    4. Mucha A, Kafarski P, Berlicki L. J. Med. Chem. 2011;54:5955. - PubMed
    5. Bhattacharya AK, Rana KC, Pannecouque C, De Clercq E. Chem Med Chem. 2012;7:1601. - PubMed

    1. Recent reviews: Ordóñez M, Rojas-Cabrera H, Cativiela C. Tetrahedron. 2009;65:17. Kudzina ZH, Kudzinb MH, Drabowiczc J, Stevens CV. Curr. Org. Chem. 2011;15:2015. Liu BJ, Cen CC, Wu MS, Kong DL. Asian. J. Chem. 2011;23:1417. Ordóñez M, Viveros-Ceballos JL, Cativiela C, Arizpe A. Curr. Org. Synth. 2012;9:310. Ordóñez M, Sayago FJ, Cativiela C. Tetrahedron. 2012;68:6369.

    1. Kabachnik MI, Medved TY. Dokl. Akad. Nauk SSSR. 1952;83:689.
    2. Fields EK. J. Am. Chem. Soc. 1952;74:1528.

    1. Selected reviews: Zefirov NS, Matveeva ED. ARKIVOC. 2008:1. Keglevich G, Balint E. Molecules. 2012;17:12821.

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