Abstract
Iron (III) triflate was used as an efficient catalyst for N-t-butoxycarbonylation of amines with di-t-butyl dicarbonate under solvent-free conditions at room temperature. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding mono-carbamates in excellent yields and short reaction times. Only two of the 23 monocarbamates were new. No competitive side reactions such as isocyanate, urea, nor N,N-di-Boc formation were observed. The reported method is mild and has the advantages of low cost, chemoselectivity and, because no solvent is used and the catalyst can be recycled, it is classifiable as a green procedure.
Keywords
References
1.
Sartori
G.
,
Ballani
R.
,
Bigi
F.
,
Bosica
G.
,
Maggi
R.
, and
Righi
P.
, Chem. Rev. , 2004 , 104 , 199 .
2.
Xiuo
X.Y.
,
Ngu
K.
,
Choa
C.
, and
Patel
D.V.
, J. Org. Chem. , 1997 , 62 , 6968 .
3.
Burk
M.J.
, and
Allen
J.G.
, J. Org. Chem. , 1997 , 62 , 7054 .
4.
Harris
R.B.
, and
Wilson
I.B.
, Tetrahedron. Lett. , 1983 , 24 , 231 .
5.
Greene
T.W.
, and
Wuts
P.G.M.
, Protecting group in organic synthesis , John Wiley and Sons , New York , 1999 .
6.
Varala
R.
,
Navula
S.
, and
Adapa
S.R.
, J. Org. Chem. , 2006 , 71 , 8283 .
7.
Pandey
R.K.
,
Ragade
S.P.
,
Upadhyay
R.K.
,
Dongare
M.K.
, and
Kumar
P.
, Arkivoc. , 2002 , VII , 28 .
8.
Sharma
G.V.M.
,
Reddy
J.J.
,
Lakshmi
P.S.
, and
Krishna
P.R.
, Tetrahedron. Lett. , 2004 , 45 , 6963 .
9.
Bartoli
G.
,
Bosco
M.
,
Locatelli
M.
,
Marcantoni
E.
,
Massaccesi
M.
,
Melchiorre
P.
, and
Sambri
L.
, Synlett. , 2004 , 10 , 1794 .
10.
Heydari
A.
, and
Hosseini
S.E.
, Adv. Synth. Catal. , 2005 , 347 , 1929 .
11.
Chankeshwara
S.
, and
Chakraborti
A.K.
, J. Mol. Catal. A Chem. , 2006 , 253 , 198 .
12.
Suryakiran
N.
,
Prabhakar
P.
,
Reddy
S.T.
,
Rajesh
K.
, and
Venkateswarlu
Y.
, Tetrahedron. Lett. , 2006 , 47 , 8039 .
13.
Shirini
F.
,
Zolfigol
M.A.
, and
Abedini
M.
, J. Iran. Chem. Soc. , 2010 , 7 , 603 .
14.
Shirini
F.
,
Mamaghani
M.
, and
Atghia
S.V.
, Catal. Commun. , 2011 , 12 , 1088 .
15.
Shirini
F.
, and
Khaligh
N.G.
, Monatsh. Chem. , 2012 , 143 , 631 .
16.
Akbari
J.
,
Heydari
A.
,
Màmani
L.
, and
Hosseini
S.H.C.R.
, C. R. Chim. , 2010 , 13 , 544 .
17.
Das
B.
,
Venkateswarlu
K.
,
Krishnaiah
M.
, and
Holla
H.
, Tetrahedron. Lett. , 2006 , 47 , 7551 .
18.
Heydari
A.
,
Shiroodi
R.K.
,
Hamidi
H.
,
Esfandyari
M.
, and
Pourayoubi
M.
, Tetrahedron. Lett. , 2007 , 48 , 5865 .
19.
Khaksar
S.
,
Vahdat
S.M.
,
Tajbakhsh
M.
,
Jahani
F.
, and
Heydari
A.
, Tetrahedron. Lett. , 2010 , 51 , 6388 .
20.
Khaksar
S.
,
Heydari
A.
,
Tajbakhsh
M.
, and
Vahdat
S.M.
, Tetrahedron. Lett. , 2008 , 49 , 3527 .
21.
Upadhyaya
D.J.
,
Barge
A.
,
Stefania
R.
, and
Cravotto
G.
, Tetrahedron. Lett. , 2007 , 48 , 8318 .
22.
Nouri
A.
,
Akbari
J.
,
Heydari
A.
, and
Nouri
A.
, Lett. Org. Chem. , 2011 , 8 , 38 .
23.
Shirini
F.
,
Atghia
S.V.
, and
Jirdehi
M.G.
, Chin. Chem. Lett. , 2013 , 24 , 34 .
24.
Shirini
F.
, and
Khaligh
N.G.
, J. Iran. Chem. Soc. , 2012 , 9 , 495 .
25.
Shirini
F.
,
Khaligh
N.G.
, and
Jolodar
O.G.
, J. Iran. Chem. Soc. , 2013 , 10 , 181 .
26.
Khaligh
N.G.
, RSC. Adv. , 2012 , 2 , 12364 .
27.
Chinnappan
A.
,
La
D.
, and
Kim
H.
, RSC. Adv. , 2013 , 3 , 13324 .
28.
Kumar
K.S.
,
Iqbal
J.
, and
Pal
M.
, Tetrahedron. Lett. , 2009 , 50 , 6244 .
29.
Knolker
H.J.
, and
Braxmeier
T.
, Tetrahedron. Lett. , 1996 , 37 , 5861 .
30.
Darnbrough
S.
,
Mervic
M.
,
Condon
S.M.
, and
Burns
C.J.
, Synth. Commun. , 2001 , 31 , 3723 .
31.
Basel
Y.
, and
Hassner
A.
, J. Org. Chem. , 2000 , 65 , 6368 .
32.
Ishihara
K.
,
Hasegama
A.
, and
Yamamoto
H.
, Angew. Chem. Int. Ed. , 2001 , 40 , 4077 .
33.
Yao
C.S.
,
Qin
B.B.
,
Zhang
H.H.
,
Lu
J.
,
Wang
D.L.
, and
Tu
S.J.
, RSC. Adv. , 2012 , 2 , 3759 .
34.
Damavandi
S.
, and
Sandaroos
R.
, Heterocycl. Commun. , 2011 , 17 , 121 .