Free accessResearch articleFirst published online 1999-12
Tetrabutylammonium Peroxydisulfate in Organic Synthesis. Part 8. 1 An Efficient and Convenient Nickel-catalyzed Oxidation of Primary Amines to Nitriles with Tetrabutylammonium Peroxydisulfate †
A series of primary amines are oxidized to the corresponding nitriles in excellent yields with tetrabutylammonium peroxydisulfate catalyzed by nickel copper formate under basic aqueous conditions.
References
1.
Part 7, ChenF. E., LiuJ. D., FuH., PengZ. Z. and ShaoL. Y., Synth. Commun., in press.
2.
NakagawaK. and TsujiT., Chem. Pharm. Bull., 1963, 11, 296;
3.
StojiljkovicA., AndrejevicV. and MihailoviM. Lj., Tetrahedron, 1967, 23, 721;
4.
ClarkeT. G., HampsonN. A., LeeJ. B., MorleyJ. R. and ScanlonB., Tetrahedron Lett., 1968, 5685;
5.
LeeJ. B., ParkjnC. and ShawM. J., Tetrahedron, 1973, 29, 751;
6.
KajimotoT., TakahashiH. and TsujiJ., J. Org. Chem., 1976, 41, 1389;
7.
KametaniT., TakahashiK., OhsawaT. and IharaM., Synthesis, 1977, 245;
8.
FeldhuesU. and SchaferH. J., Synthesis, 1982, 145;
9.
TangR., DiamondS. E., NearyN. and MaresF., J. Chem. Soc., Chem. Commun., 1978, 562;
10.
CeniniS., PortaF. and PizzottioM., J. Mol. Catal., 1982, 15, 297;
11.
PortaF., GrottiC., CeniniS. and PalmisanoG., J. Mol. Catal., 1989, 50, 333;
12.
GreenG., GriffithW. P., HollmsheadD. M., LeyS. V. and SchroderM., J. Chem. Soc., Perkin Trans. 1, 1984, 681;
13.
YamazakiS. and YamazakiY., Bull. Chem. Soc. Jpn., 1990, 63, 301;
14.
CapdevielleP., LavigneA. and MaumyM., Synthesis, 1989, 451.
15.
SemmelhackM. F. and SchmidC. R., J. Am. Chem. Soc., 1983, 105, 6732;
16.
BarnesK. K. and MannC. K., J. Org. Chem., 1967, 32, 1474;
17.
HampsonN. A., LeeJ. B. and MacDonaldK. I., Electrochim Acta, 1972, 17, 921;
18.
BlackhamA. U., KurakS. and PalmerJ. L., J. Electrochem. Soc., 1975, 212, 1081;
19.
FeldhuesU. and SchaferH. J., Synthesis, 1982, 145;
20.
ShonoT., MatsumuraY. and InoueK., J. Am. Chem. Soc., 1984, 106, 6075.
21.
JungJ. C., ChaiH. C. and KimY. H., Tetrahedron Lett., 1993, 34, 3581;
22.
ChoiH. C. and KimY. H., Synth. Commun., 1994, 24, 2307;
23.
ChenF. E., YangJ. S., ZhangH., GuanC. S. and WanJ. L., Synth. Commun., 1995, 25, 3163;
24.
ChenF. E.LiuA. C., YanQ. J., LiuM. X., ZhangD. M. and ShaoL. Y., Synth. Commun., 1999, 291049;
25.
ChenF. E., WanJ. L., GuanC. S., YangJ. S. and ZhangH., Synth. Commun., 1996, 26, 253.
26.
Sampath KumarH. M., MohantyP. K., Suresh KumarM. and YadavJ. S., Synth. Commun., 1997, 27, 1327.
27.
CorreiaJ., Synthesis, 1994, 1127.
28.
Sampath KumarH. M., Subba ReddyB. V., Tiyupathi ReddyP. and YadavJ. S., Synthesis, 1999, 587.
29.
SaednyaA., Synthesis, 1985, 184.
30.
MeshramH. M., Synthesis, 1992, 943.
31.
KokelB., MenichiG. and Hubert-HabartM., Synthesis, 1985, 201.
