Abstract
The addition of Grignard reagents to highly hindered acylferrocenes in the presence of anhydrous CeCl3 at room temperature provided the corresponding α-ferrocenyl tertiary alcohols FcC(OH)R1R2 (R1 = Ph or Fc, R2 = Me, Et, i Pr, n Bu, Ph; Fc = C5H4FeC5H5) in moderate to high yields. Optimum conditions and factors affecting the reaction were investigated.
References
1.
Ferguson
G.
,
Glidewell
C.
,
Opromolla
G.
,
Zakaria
C.M.
, and
Zanello
P.
, J. Organomet. Chem. , 1996 , 506 , 129 .
2.
Joubert
C.C.
,
van As
L.
,
Jakob
A.
,
Speck
J.M.
,
Lang
H.
, and
Swarts
J.C.
, Polyhedron , 2013 , 55 , 80 .
3.
Zhao
H.Y.
,
Guo
L.
,
Chen
S.F.
, and
Bian
Z.X.
, J. Mol. Struct. , 2013 , 1054 , 164 .
4.
Li
P.Z.
, and
Liu
Z.Q.
, Eur. J. Med. Chem. , 2011 , 46 , 1821 .
5.
Purecha
V.H.
,
Nandurkar
N.S.
,
Bhanage
B.M.
, and
Nagarkar
J.M.
, Tetrahedron Lett. , 2008 , 49 , 5252 .
6.
Romero
T.
,
Orenes
R.A.
,
Tárraga
A.
, and
Molina
P.
, Organometallics , 2013 , 32 , 5740 .
7.
Ganesh
V.
,
Sudhir
V.S.
,
Kundu
T.
, and
Chandrasekaran
S.
, Chem. Asian J. , 2011 , 6 , 2670 .
8.
Zhao
H.Y.
,
Guo
L.
,
Chen
S.F.
, and
Bian
Z.X.
, RSC Adv. , 2013 , 3 , 19929 .
9.
Jiang
R.
,
Yuan
C.X.
,
Xu
X.P.
, and
Ji
S.J.
, Appl. Organometal. Chem. , 2012 , 26 , 62 .
10.
Cozzi
P.G.
, and
Zoli
L.
, Green Chem. , 2007 , 9 , 1292 .
11.
Wu
Y.
,
Lu
C.
,
Shan
W.
, and
Li
X.
, Tetrahedron: Asymmetr. , 2009 , 20 , 584 .
12.
Jiang
R.
,
Zhang
Y.
,
Shen
Y.C.
,
Zhu
X.
,
Xu
X.P.
, and
Ji
S.J.
, Tetrahedron , 2010 , 66 , 4073 .
13.
Ueberbacher
B.J.
,
Griengl
H.
, and
Weber
H.
, Chem. Commun. , 2008 , 28 , 3287 .
14.
Tang
Z.Y.
,
Lu
Y.
, and
Hu
Q.S.
, Org. Lett. , 2003 , 5 , 297 .
15.
Glidewell
C.
,
Klar
R.B.
,
Lightfoot
P.
,
Zakaria
C.M.
, and
Ferguson
G.
, Acta Cryst. , 1996 , B52 , 110 .
16.
Ferguson
G.
, and
Gallagher
J.F.
, Acta Cryst. , 1993 , C49 , 967 .
17.
Carollo
L.
,
Curulli
A.
, and
Floris
B.
, Appl. Organomet. Chem. , 2003 , 17 , 589 .
18.
Asahara
M.
,
Natsume
S.
,
Kurihara
H.
,
Yamaguchi
T.
,
Erabi
T.
, and
Wada
M.
, J. Organomet. Chem. , 2000 , 601 , 246 .
19.
Rebiere
F.
,
Samuel
O.
, and
Kagan
H.B.
, Tetrahedron Lett. , 1990 , 31 , 3121 .
20.
Ferguson
G.
, and
Gallagher
J.F.
, J. Organomet. Chem. , 1994 , 464 , 95 .
21.
Boev
V.I.
, and
Dombrovskii
A.V.
, Zh. Org. Khim. , 1983 , 19 , 895 .
22.
Boev
V.I.
, and
Dombrovskii
A.V.
, Zh. Obshch. Khim. , 1984 , 54 , 970 .
23.
Bunton
C.A.
,
Carrasco
N.
, and
Watts
W.E.
, J. Organomet. Chem. , 1977 , 131 , C21 .
24.
Milos
D.
,
Stanimir
K.
,
Vladimir
P.
,
Jasmina
P.
,
Zoran
R.
,
Anna
R.
, and
Svetlana
S.
, J. Serb. Chem. Soc. , 1995 , 60 , 737 .
25.
Wu
K.L.
,
Sokolova
E.B.
,
Chlenov
I.E.
, and
Petrov
A.D.
, Dokl. Akad. Nauk SSSR , 1961 , 137 , 111 .
26.
Bozak
R.E.
,
Riley
R.G.
,
Fawns
W.P.
, and
Javaheripour
H.
, Chem. Lett. , 1974 , 2 , 167 .
27.
Jain
R.P.
, and
Williams
R.M.
, J. Org. Chem. , 2002 , 63 , 6361 .
28.
Takahashi
S.
, and
Nakata
T.
, J. Org. Chem. , 2002 , 63 , 5739 .
29.
Matsukawa
S.
,
Funabashi
Y.
, and
Imamoto
T.
, Tetrahedron Lett. , 2003 , 44 , 1007 .
30.
Imamoto
T.
,
Takiyama
N.
,
Nakamura
K.
,
Hatajima
T.
, and
Kamiya
Y.
, J. Am. Chem. Soc. , 1989 , 111 , 4392 .
31.
Bian
Z.X.
,
Zhao
H.Y.
, and
Li
B.G.
, Polyhedron , 2003 , 22 , 1523 .
32.
Bunton
C.A.
,
Carrasco
N.
,
Cully
N.
, and
Watts
W.E.
, J.C.S. Perkin I1 , 1980 , 12 , 1859 .
33.
Pauson
P. L.
, and
Watts
W.E.
, J. Chem. Soc. , 1962 , 3880 .
