Abstract
Oxidative α-cyanation of tertiary amines was achieved by using an MCM-41-immobilised N-alkylethylenediamine ruthenium(III) complex (MCM-41-2N-RuCl3) as catalyst in MeOH at 60 °C in the presence of H2O2 as oxidant and NaCN in acetic acid as a cyanide source to afford the corresponding α-aminonitriles in good yields. The new heterogeneous ruthenium catalyst can easily be prepared by a simple two-step procedure from commercially readily available and inexpensive reagents. It can be recovered by filtration of the reaction solution and reused at least 7 times without significant loss of activity.
Keywords
References
1.
Ritleng V.
,
Sirlin C.
, and
Pfeffer M.
, Chem. Rev. , 2002 , 102 , 1731 .
2.
En D.
,
Zou G.-F.
,
Guo Y.
, and
Liao W.-W.
, J. Org. Chem. , 2014 , 79 , 4456 .
3.
North M.
, Comprehensive organic functional group transformations , eds
Katritzky A.R.
,
Meth-Cohn O.
,
Rees C.W.
, and
Pattenden G.
Pergamon , Oxford , 1995 , Vol. 3 , pp. 611 –617 .
4.
Surendra K.
,
Krishnaveni N.S.
,
Mahesh A.
, and
Rao K.R.
, J. Org. Chem. , 2006 , 71 , 2532 .
5.
Barton D.H.R.
,
Billion A.
, and
Boivin J.
, Tetrahedron Lett. , 1985 , 26 , 1229 .
6.
Chen C.-K.
,
Hortmann A.G.
, and
Marzabadi M.R.
, J. Am. Chem. Soc. , 1988 , 110 , 4829 .
7.
Wagner A.
, and
Ofial A.R.
, J. Org. Chem. , 2015 , 80 , 2848 .
8.
Vu V.H.
,
Louafi F.
,
Girard N.
,
Marion R.
,
Roisnel T.
,
Dorcet V.
, and
Hurvois J.-P.
, J. Org. Chem. , 2014 , 79 , 3358 .
9.
Murahashi S.I.
,
Komiya N.
,
Terai H.
, and
Nakae T.
, J. Am. Chem. Soc. , 2003 , 125 , 15312 .
10.
Murahashi S.I.
,
Komiya N.
, and
Terai H.
, Angew. Chem., Int. Ed. , 2005 , 44 , 6931 .
11.
Murahashi S.I.
,
Nakae T.
,
Terai H.
, and
Komiya N.
, J. Am. Chem. Soc. , 2008 , 130 , 11005 .
12.
Kumar P.
,
Varma S.
, and
Jain S.L.
, J. Mater. Chem. A , 2014 , 2 , 4514 .
13.
Varma S.
,
Jain S.L.
, and
Sain B.
, ChemCatChem , 2011 , 3 , 1329 .
14.
Reddy K.H.V.
,
Satish G.
,
Reddy V.P.
,
Kumar B.S.P.A.
, and
Nageswar Y.V.D.
, RSC Adv. , 2012 , 2 , 11084 .
15.
Han W.
, and
Ofial A.R.
, Chem. Commun. , 2009 , 5024 .
16.
Singhal S.
,
Jain S.L.
, and
Sain B.
, Adv. Synth. Catal. , 2010 , 352 , 1338 .
17.
Panwar V.
,
Kumar P.
,
Bansal A.
,
Ray S.S.
, and
Jain S.L.
, Appl. Catal., A , 2015 , 498 , 25 .
18.
Liu P.
,
Liu Y.
,
Wong E.L.
,
Xiang S.
, and
Che C.-M.
, Chem. Sci. , 2011 , 2 , 2187 .
19.
Singhal S.
,
Jain S.L.
, and
Sain B.
, Chem. Commun. , 2009 , 2371 .
20.
Alagiri K.
, and
Prabhu K.R.
, Org. Biomol. Chem. , 2012 , 10 , 835 .
21.
Zhang Y.
,
Peng H.
,
Zhang M.
,
Cheng Y.
, and
Zhu C.
, Chem. Commun. , 2011 , 47 , 2354 .
22.
Yang W.
,
Wei L.
,
Yi F.
, and
Cai M.
, Tetrahedron , 2016 , 72 , 4059 .
23.
Lin A.
,
Peng H.
,
Abdukader A.
, and
Zhu C.
, Eur. J. Org. Chem. , 2013 , 7286 .
24.
Cole-Hamilton D.J.
, Science , 2003 , 299 , 1702 .
25.
Kresge C.T.
,
Leonowicz M.E.
,
Roth W.J.
,
Vartuli J.C.
, and
Beck J.S.
, Nature , 1992 , 359 , 710 .
26.
Martin-Aranda R.M.
, and
Cejka J.
, Top. Catal. , 2010 , 53 , 141 .
27.
Mehnert P.C.
,
Weaver D.W.
, and
Ying J.Y.
, J. Am. Chem. Soc. , 1998 , 120 , 12289 .
28.
Mukhopadhyay K.
,
Sarkar B.R.
, and
Chaudhari R.V.
, J. Am. Chem. Soc. , 2002 , 124 , 9692 .
29.
Cai M.
,
Peng J.
,
Hao W.
, and
Ding G.
, Green Chem. , 2011 , 13 , 190 .
30.
Shyu S.-G.
,
Cheng S.-W.
, and
Tzou D.-L.
, Chem. Commun. , 1999 , 2337 .
31.
Jia M.
,
Seifert A.
, and
Thiel W.R.
, Chem. Mater. , 2003 , 15 , 2174 .
32.
Villaverde G.
,
Corma A.
,
Iglesias M.
, and
Sanchez F.
, ACS Catal. , 2012 , 2 , 399 .
33.
Zhao H.
,
He W.
,
Yao R.
, and
Cai M.
, Adv. Synth. Catal. , 2014 , 356 , 3092 .
34.
Cai M.
,
Yao R.
,
Chen L.
, and
Zhao H.
, J. Mol. Catal. A: Chem. , 2014 , 395 , 349 .
35.
Zhao H.
,
He W.
,
Wei L.
, and
Cai M.
, Catal. Sci. Technol. , 2016 , 6 , 1488 .
36.
Lempers H.E.B.
, and
Sheldon R.A.
, J. Catal. , 1998 , 175 , 62 .
37.
Lim M.H.
, and
Stein A.
, Chem. Mater. , 1999 , 11 , 3285 .
38.
Zhang G.
,
Ma Y.
,
Cheng G.
,
Liu D.
, and
Wang R.
, Org. Lett. , 2014 , 16 , 656 .
39.
Wagner A.
,
Han W.
,
Mayer P.
, and
Ofial A.R.
, Adv. Synth. Catal. , 2013 , 355 , 3058 .