Abstract
An environmentally friendly catalytic system of Fe2(SO4)3/4-OH-TEMPO/NaNO2 has been developed for aerobic oxidation of alcohols to aldehydes and ketones. The catalytic system allowed efficient and selective oxidation of a wide range of alcohols using oxygen at 1 atmospheric pressure and room temperature. 100% selectivity and excellent conversion rates were observed for benzylic alcohols and cinnamyl alcohol.
References
1.
Arends I.W.C.E.
, and
Sheldon R.A.
, Modern oxidation methods , 2nd edn. Wiley-VCH Verlag GmbH&Co. KGaA , Weinheim, Germany , 2010 , pp. 147 –185 .
2.
Schultza M.J.
, and
Sigman M.S.
, Tetrahedron , 2006 , 62 , 8227 .
3.
Jiang N.
, and
Ragauskas A.J.
, Tetrahedron Lett. , 2007 , 48 , 273 .
4.
Holum J.R.
, J. Org. Chem. , 1961 , 26 , 4814 .
5.
Highet R.J.
, and
Wildman W.C.
, J. Am. Chem. Soc. , 1955 , 77 , 4399 .
6.
Cella J.A.
,
Kelley J.A.
, and
Kenehan E.F.
, J. Org. Chem. , 1975 , 40 , 1860 .
7.
Ganern B.
, J. Org. Chem. , 1975 , 40 , 1998 .
8.
Dijksman A.
,
Marino-Gonzalez A.
,
Mairata i Payeras A.
,
Arends I.W.C.E.
, and
Sheldon R.A.
, J. Am. Chem. Soc. , 2001 , 123 , 6826 .
9.
Hoover J.M.
, and
Stahl S.S.
, J. Am. Chem. Soc. , 2011 , 133 , 16901 .
10.
Wang N.W.
,
Liu R.H.
,
Chen J.P.
, and
Liang X.M.
, Chem. Commun. , 2005 , 42 , 5322 .
11.
Yin W.L.
,
Chu C.H.
,
Lu Q.Q.
,
Tao J.W.
,
Liang X.M.
, and
Liu R.H.
, Adv. Synth. Catal. , 2010 , 352 , 113 .
12.
Wang L.Y.
,
Li J.
,
Lv Y.
,
Zhao G.D.
, and
Gao S.
, Appl. Organometal. Chem. , 2012 , 26 , 37 .
13.
Ma S.M.
,
Liu J.X.
,
Li S.H.
,
Chen B.
,
Cheng J.J.
,
Kuang J.Q.
,
Liu Y.
,
Wan B.Q.
,
Wang Y.L.
,
Ye J.T.
,
Yu Q.
,
Yuan W.M.
, and
Yu S.C.
, Adv. Synth. Catal. , 2011 , 353 , 1005 .
14.
Liu J.X.
,
Xie X.
, and
Ma S.M.
, Synthesis , 2012 , 44 , 1569 .
15.
Tamura N.
,
Aoyama T.
,
Takido T.
, and
Kodomari M.
, Synlett , 2012 , 23 , 1397 .
16.
Zheng C.G.
,
Liu X.Y.
,
Peng F.F.
,
Yu X.W.
, and
Xu Y.
, CN patent , 102093182, 2011.
17.
Wang Q.F.
,
Zhang Y.
,
Zheng G.G.
,
Tian Z.Z.
, and
Yang G.Y.
, Catal. Commun. , 2011 , 14 , 92 .
18.
Hu Z.Z.
, and
Kerton F.M.
, Appl. Catal. A-Gen. , 2012 , 413–414 , 332 .
19.
Gamez P.
,
Arends I.W.C.E.
,
Sheldon R.A.
, and
Reedijk J.
, Adv. Synth. Catal. , 2004 , 346 , 805 .
20.
Scepaniak J.J.
,
Wright A.M.
,
Lewis R.A.
,
Wu G.
, and
Hayton T.W.
, J. Am. Chem. Soc. , 2012 , 134 , 19350 .
21.
Hajipour A.R.
,
Mostafavi M.
, and
Ruoho A.E.
, Monatsh. Chem. , 2007 , 138 , 569 .
22.
Suzuki T.
,
Morita K.
,
Tsuchida M.
, and
Hiroi K.
, J. Org. Chem. , 2003 , 68 , 1601 .
23.
Qian W.X.
,
Jin E.L.
,
Bao W.L.
, and
Zhang Y.M.
, Angew. Chem. Int. Edit. , 2005 , 44 , 952 .