Abstract
A convenient method for direct oxidative conversion of aldehydes and alcohols into nitriles has been developed by using the inexpensive and environmentally friendly reagent I2/aqueous NH4OAc. The aqueous NH4OAc as a nontoxic cyanide source is more eco-friendly than aqueous ammonia, because gaseous ammonia evaporates easily from aqueous ammonia but not from aqueous NH4OAc.
References
1.
Liu K.C.
, and
Howe R.K.
, J. Org. Chem. , 1983 , 48 , 4590 .
2.
Harris T.M.
,
Harris C.M.
,
Oster T.A.
,
Brown L.E.
, and
Lee J.Y.C.
, J. Am. Chem. Soc. , 1988 , 110 , 6180 .
3.
Labrock R.C.
, Comprehensive Organic Transformations , VCH , New York , 1989 . pp. 819 –995 .
4.
Sundermeier M.
,
Zapf A.
,
Mutyala S.
,
Baumann W.
,
San J.
,
Weiss S.
, and
Beller M.
, Chem. Eur. J. , 2003 , 9 , 1828 .
5.
Zanon J.
,
Klapars A.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2003 , 125 , 2890 .
6.
Jensen M.L.
,
Gajare A.S.
,
Toyota K.
,
Yoshijuji M.
, and
Ozawa F.
, Tetrahedron Lett. , 2005 , 46 , 8645 .
7.
Lin L.S.
,
Fors B.P.
, and
Chobanian H.R.
, Tetrahedron Lett. , 2006 , 47 , 3303 .
8.
Li L.-H.
,
Pan Z.-L.
, and
Liang Y.-M.
, Synlett , 2006 , 2094 .
9.
Schareina T.
,
Zapf A.
,
Magerlein W.
,
Muller N.
, and
Beller M.
, Tetrahedron Lett. , 2007 , 48 , 1087 .
10.
Sakaibara Y.
,
Okuda F.
,
Shimoyabashi A.
,
Ido Y.
,
Sakai K.
,
Sakai M.
, and
Uchino N.
, Bull. Chem. Soc. Jpn , 1993 , 66 , 2776 .
11.
Percec V.
,
Bae J.-Y.
, and
Hill D.H.
, J. Org. Chem. , 1995 , 60 , 6895
12.
Leadbeater N.E.
, and
Arvela R.K.
, J. Org. Chem. , 2003 , 68 , 9122 .
13.
Yan P.
,
Batamack P.
,
Prakash G.K.S.
, and
Olah G.A.
, Catal. Lett. , 2005 , 101 , 141 .
14.
Misono A.
,
Osa T.
, and
Koda S.
, Bull. Chem. Soc. Jpn , 1966 , 39 , 854 .
15.
Okimoto M.
, and
Chiba T.
, J. Org. Chem. , 1988 , 53 , 218 .
16.
Erman M.B.
,
Snow J.W.
, and
Williams M.J.
, Tetrahedron Lett. , 2000 , 41 , 6749 .
17.
Talukdar S.
,
Hsu J.L.
,
Chou T.C.
, and
Fang J.M.
, Tetrahedron Lett. , 2001 , 42 , 1103 .
18.
Mori N.
, and
Togo H.
, Synlett , 2005 , 1456 .
19.
Tian X.
,
Tan S.P.
,
Teo W.K.
, and
Li K.
, J. Membr. Sci. , 2006 , 271 , 59 .
20.
Das B.
,
Ramesh C.
, and
Madhusudhan P.
, Synlett , 2000 , 1599 .
21.
Srinivas K.V.N.S.
,
Reddy E.B.
, and
Das B.
, Synlett , 2002 , 625 .
22.
Gaikwad D.D.
,
Renukdas S.V.
,
Kendre B.V.
,
Shisodia S.U.
,
Borade R.M.
,
Shinde P.S.
,
Chaudhary S.S.
, and
Pawar R.P.
, Synth. Commun. , 2007 , 37 , 257 .
23.
Weiss M.
, J. Am. Chem. Soc. , 1952 , 74 , 5193 .
24.
Ko S.
,
Sastry M.N.O.
,
Lin C.
, and
Yao C.F.
, Tetrahedron Lett. , 2005 , 46 , 5771 .
25.
Heravi M.M.
,
Bakhtiari K.
,
Daroogheha Z.
, and
Bamoharram F.F.
, Catal. Commun. , 2005 , 8 , 1991 .
26.
Kidwai M.
, and
Mothsra P.
, Tetrahedron Lett. , 2006 , 47 , 5029 .
27.
Zhu Y.Z.
, and
Cai C.
, J. Chem. Res. , 2007 , 484 .
28.
Zhu Y.Z.
, and
Cai C.
, Synth. Commun. , 2007 , 37 , 3359 .
29.
Zhu Y.Z.
, and
Cai C.
, Eur. J. Org. Chem. , 2007 , 2401 .
30.
Ren Y.M.
, and
Cai C.
, Synth. Commun. , 2007 , 37 , 2209 .
31.
Ren Y.M.
, and
Cai C.
, Catal. Lett. , 2007 , 118 , 134 .
32.
Ren Y.M.
, and
Cai C.
, Catal. Commun. , 2008 , 9 , 1017 .
33.
Iida S.
, and
Togo H.
, Tetrahedron , 2007 , 63 , 8274 .
34.
Pollack J. R. A.
, and
Stevens R.
, Dictionary of Organic Compounds ; Eyre and Spottiswoode Ltd : Great Britain , 1965 .
35.
Online data from Sigma-Aldrich; http://www.sigamaaldrich.com/Brands/Aldrich.html
36.
Roesky H. W.
, and
Möckel K.
, Chemical Curiosities , VCH , Weinheim , 1996 , pp. 292 –293 .
