Abstract
Cyanation of aryl bromides were carried out with K4[Fe(CN)6] in the presence of catalytic amounts of a copper salt and 1,2-bis(5-tetrazolyl)benzene as a ligand under thermal conditions. This method has the advantages of high yields, simple methodology and easy work up.
References
1.
Larock R.C.
, Comprehensive organic transformations. VCH , New York , 1989 , p. 819 .
2.
Rappoport Z.
, Chemistry of the cyano group. John Wiley & Sons , London , 1970 , p. 121 .
3.
Nasrollahzadeh M.
,
Bayat Y.
,
Habibi D.
, and
Moshaee S.
, Tetrahedron Lett. , 2009 , 50 , 4435 .
4.
Habibi D.
,
Nasrollahzadeh M.
,
Sahebekhtiari H.
, and
Sajadi S.M.
, Synlett , 2012 , 23 , 2795 .
5.
Habibi D.
,
Nasrollahzadeh M.
,
Sahebekhtiari H.
, and
Parish R.V.
, Tetrahedron , 2013 , 69 , 3082 .
6.
Nasrollahzadeh M.
,
Ehsani A.
, and
Rostami-Vartouni A.
, Ultrason. Sonochem. , 2014 , 21 , 275 .
7.
Nasrollahzadeh M.
,
Habibi D.
,
Shahkarami Z.
, and
Bayat Y.
, Tetrahedron , 2009 , 66 , 3866 .
8.
Habibi D.
, and
Nasrollahzadeh M.
, Synth. Commun. , 2010 , 40 , 3159 .
9.
Habibi D.
, and
Nasrollahzadeh M.
Synth. Commun. , 2012 , 42 , 2023 .
10.
Habibi D.
, and
Nasrollahzadeh M.
,
Bayat Y.
, Synth. Commun. , 2011 , 41 , 2135 .
11.
Habibi D.
, and
Nasrollahzadeh M.
, Monatsh. Chem. , 2012 , 143 , 925 .
12.
Habibi D.
,
Nasrollahzadeh M.
,
Faraji A.R.
, and
Bayat Y.
, Tetrahedron , 2010 , 66 , 3866 .
13.
Habibi D.
,
Nasrollahzadeh M.
, and
Sahebekhtiari H.
, J. Mol. Catal. A: Chem. , 2013 , 378 , 148 .
14.
Ellis G.P.
, and
Romney-Alexander T.M.
, Chem. Rev. , 1987 , 87 , 779 .
15.
Sandmeyer T.
, Berichte der Deutschen Chemischen Gesellschaft , 1884 , 17 , 2650 .
16.
Habibi D.
,
Heydari S.
, and
Nasrollahzadeh M.
, J. Chem. Res. , 2012 , 36 , 573 .
17.
Chatani N.
, and
Hanafusa T.
, J. Org. Chem. , 1986 , 51 , 4714 .
18.
Zieger H.E.
, and
Wo S.
, J. Org. Chem. , 1994 , 59 , 3838 .
19.
Chobanian H.R.
,
Fors B.P.
, and
Lin L.S.
, Tetrahedron Lett. , 2006 , 47 , 3303 .
20.
Jensen R.S.
,
Gajare A.S.
,
Toyota K.
, and
Yoshifujia M.
F. Tetrahedron Lett. , 2005 , 46 , 8645 .
21.
Hatsuda M.
, and
Seki M.
, Tetrahedron , 2005 , 61 , 9908 .
22.
Schareina T.
,
Zapf A.
, and
Beller M.
, Chem. Commun. , 2004 , 1388 .
23.
Nandurkar N.S.
, and
Bhanage B.M.
, Tetrahedron , 2008 , 64 , 3655 .
24.
Cheng Y.-N.
,
Duan Z.
,
Yu L.
,
Li Z.
,
Zhu Y.
, and
Wu Y.
, Org. Lett. , 2008 , 10 , 901 .
25.
Littke A.
,
Soumeillant M.
,
Kaltenbach R.F.
III
,
Cherney R.J.
,
Tarby C.M.
, and
Kiau S.
, Org. Lett. , 2007 , 9 , 1711 .
26.
Zanon J.
,
Klapars A.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2003 , 125 , 2890 .
27.
Schareina T.
,
Zapf A.
, and
Beller M.
, Tetrahedron Lett. , 2005 , 46 , 2585 .
28.
Bourissou D.
,
Guerret O.
,
Gabbai F.P.
, and
Betrand G.
, Chem. Rev. , 2000 , 100 , 39 .
29.
McGuiness D.S.
,
Saendig N.
,
Yates B.F.
, and
Carvell K.J.
, J. Am. Chem. Soc. , 2001 , 123 , 4029 .
30.
Habibi D.
,
Nasrollahzadeh M.
,
Mehrabi L.
, and
Mostafaee S.
, Monatsh. Chem. , 2013 , 144 , 725 .
31.
Habibi D.
,
Nabavi H.
, and
Nasrollahzadeh M.
, J. Chem. , 2013 , Article ID 645313.
32.
Habibi D.
,
Nasrollahzadeh M.
, and
Kamali T.A.
, Green Chem. , 2011 , 13 , 3499 .
33.
Shahroosvand H.
,
Najafi L.
,
Mohajerani E.
,
Khabbazi A.
, and
Nasrollahzadeh M.
, J. Mater. Chem. C , 2013 , 1 , 1337 .
34.
Shahroosvand H.
,
Najafi L.
,
Mohajerani E.
,
Janghouri M.
, and
Nasrollahzadeh M.
, RSC Adv. , 2013 , 3 , 6323 .
35.
Demko Z.P.
,
Sharpless K.B.
, J. Org. Chem. , 2001 , 66 , 7945 .
36.
Diez-Barra E.
,
Guerra J.
,
Lopez-Solera I.
,
Marino S.
,
Rodriguez-Lopez J.
,
Sanchez-Verdu P.
, and
Tejeda J.
, Organometallics , 2003 , 22 , 541 .
37.
Nasrollahzadeh M.
,
Rostami-Vartooni A.
,
Ehsani A.
, and
Moghadam M.
, J. Mol. Catal. A: Chem. , 2014 , 387 , 123 .
38.
Xu H.-J.
,
Liang Y.-F.
,
Zhou X.-F.
, and
Feng Y.-S.
, Org. Biomol. Chem. , 2012 , 10 , 2562 .
39.Aldrich Handbook of Fine Chemicals and Laboratory Equipment. Sigma Aldrich .
40.
Zanon J.
,
Klapars A.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2003 , 125 , 2890 .