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bS Supporting Information
ABSTRACT: A Cu(I)-catalyzed cross-coupling reaction leading to the
synthesis of N-alkynylheteroarenes from 1,1-dibromo-1-alkenes is described.
Generally superior yields and functional group tolerance were obtained with
TMEDA as ligand using imidazole and benzimidazole substrates in dioxane.
Received:
NOTE
yield (%)c
entry
catalyst (%)
ligandb
base (equiv)
solvent
T (C)
3a
CuI (5)
DMEDA
Cs2CO3 (4)
dioxane
60
41
CuI (5)
DMEDA
Cs2CO3 (4)
dioxane
80
66
CuI (5)
TMEDA
Cs2CO3 (4)
dioxane
80
82
CuI (5)
TMEDA
Cs2CO3 (4)
dioxane
102 (reux)
67
14
CuI (5)
TMEDA
Cs2CO3 (4)
dioxane
60
40
6
7
CuI (2.5)
TMEDA
Cs2CO3 (4)
Cs2CO3 (4)
dioxane
dioxane
80
80
45
0
0
0
CuI (10)
TMEDA
Cs2CO3 (4)
dioxane
80
77
CuI (5)
TMEDA
Cs2CO3 (6)
dioxane
80
79
trace
10
CuI (5)
TMEDA
Cs2CO3 (3)
dioxane
80
65
11d
CuI (5)
TMEDA
Cs2CO3 (2)
dioxane
80
29
12
CuI (5)
TMEDA
Cs2CO3 (4)
DMF
80
50
12
13
CuI (5)
TMEDA
Cs2CO3 (4)
toluene
80
27
14
15
CuI (5)
CuI (5)
TMEDA
TMEDA
K2CO3 (4)
K3PO4 (4)
dioxane
dioxane
80
80
0
73
0
4
16
Cu (5)
TMEDA
Cs2CO3 (4)
dioxane
80
17
CuO (5)
TMEDA
Cs2CO3 (4)
dioxane
80
trace
18
CuCl (5)
TMEDA
Cs2CO3 (4)
dioxane
80
19
23
Reactions were carried out using imidazole (1 mmol), (2,2-dibromovinyl)benzene (1.5 mmol), and ligand (0.1 mmol) in 2 mL of solvent for 24 h under
N2. b TMEDA = N,N,N0 ,N0 -tetramethylethylenediamine; DMEDA = N,N0 -dimethylethanediamine. c Yields of isolated products after chromatographic
purication. d Reaction run at 80 C for 48 h.
reaction time (entry 10, Table 2). We found, however, that vinyl
1,1-dibromoalkenes such as 1,1-dibromo-4-methylpenta-1,3diene, which are denitely not the best reaction partners in
copper-catalyzed cross-coupling reactions, were not suitable
substrates (entry 11, Table 2).
The coupling of imidazoles bearing dierent substituents with
various 1,1-dibromo-1-alkenes 2 was investigated next under the
optimized reaction conditions (Table 3). In general, the substituted imidazoles could be successfully used in this coppermediated cross-coupling reaction to give the desired products in
moderate to good yields. For example, when 2-methylimidazole
was used, good yields of the N-alkynylheteroarenes derived from
the coupling of the 1,1-dibromoalkenes 2a, 2b, and 2d were
observed (entries 68, Table 3). The reaction was, however,
found to be rather general and allowed for the synthesis of a wide
range of N-alkynylimidazoles possessing ethyl, propyl, isopropyl,
and benzo[d] substituting groups. In the case of 4-methylimidazole (entry 20, Table 3), coupling with 2a gave a 7:1 mixture of
regioisomeric N-alkynylimidazoles 5ta and 5tb. The regiochemistry of the major isomer 5ta was established as 1,4 by NMR.
The plausible mechanism for this transformation is depicted
in Scheme 1. The sequence begins with the deprotonation of the
imidazole by Cs2CO3 followed by cesiumcopper transmetalation to generate a copper(I)(imidazolate) intermediate B. Then,
two hypotheses both involving the formation of a copper(III)
complex C or D could be considered.13 Path 1 involves the Nalkenylation of imidazole on the more reactive trans CBr bond
of the gem-dibromoolen to furnish the trisubstituted alkene E.
Dehydrobromination takes place at the late stage to generate
NOTE
a
1a (1.0 mmol) and 2 (1.5 mmol) at 80 C for 24 h, under N2. b Yields of
isolated products after chromatographic purication. c Reaction run at
60 C. d Reaction run at 80 C for 48 h. e No reaction.
EXPERIMENTAL SECTION
General Methods. All reactions were carried out under nitrogen in
oven-dried glassware with magnetic stirring. Unless otherwise noted, all
materials were obtained from commercial suppliers and were used without
further purification. 1,1-Dibromo-1-alkenes 2al were prepared according
to the reported procedures.11c All solvents were reagent grade. 1,4-Dioxane
was freshly distilled from sodium/benzophenone under nitrogen prior to
use. Dichloromethane and toluene were freshly distilled from CaH2 prior
to use. DMF was dried over 4 molecular sieves overnight prior to use.
Unless otherwise noted, organic extracts were dried with Na2SO4, filtered
C
NOTE
NOTE
Table 3. Continued
1 (1.0 mmol) and 2 (1.5 mmol) at 80 C for 24 h, under N2. b Yields of isolated products after chromatographic purication. c GC yield, with 1-methyl1H-imidazole as the internal standard. d The ratio of the isomeric products was determined by GC. e Reaction run at 80 C for 48 h.
a
114.4, 113.0, 77.1, 70.4, 55.5; MS (ESI) m/z 199.0 ([M H]); HRMS
(EI) calcd for C12H10N2O (M) 198.0793, found 198.0792.
1-((4-Fluorophenyl)ethynyl)-1H-imidazole (3g): yellow oil;
1
H NMR (500 MHz, CDCl3) 7.81 (s, 1H), 7.537.44 (m, 2H), 7.19
(s, 1H), 7.117.02 (m, 3H); 13C NMR (125 MHz, CDCl3) 164.1,
162.1, 140.2, 134.03, 134.0, 129.5, 121.9, 117.3, 116.2, 116.1, 78.0, 69.6;
MS (ESI) m/z 187.0 ([M H]); HRMS (EI) calcd for C11H7FN2
(M) 186.0593, found 186.0598.
1-(Furan-2-ylethynyl)-1H-imidazole (3h). yellow oil; 1H NMR
(500 MHz, CDCl3) 7.837.78 (m, 1H), 7.48 (dd, J = 1.9, 0.7 Hz, 1H),
7.19 (t, J = 1.3 Hz, 1H), 7.09 (dd, J = 1.4, 0.8 Hz, 1H), 6.74 (dd, J = 3.4,
0.7 Hz, 1H), 6.46 (dd, J = 3.4, 1.9 Hz, 1H); 13C NMR (125 MHz,
CDCl3) 144.9, 140.6, 135.5, 129.8, 122.1, 117.7, 111.5, 82.0, 61.8; MS
(ESI) m/z 158.9 ([M H]); HRMS (EI) calcd for C9H6N2O (M)
158.0480, found 158.0469.
1-(Thiophen-2-ylethynyl)-1H-imidazole (3i). white solid; mp
4648 C; 1H NMR (500 MHz, CDCl3) 7.80 (s, 1H), 7.36 (dd,
J = 5.2, 1.0 Hz, 1H), 7.32 (dd, J = 3.6, 1.0 Hz, 1H), 7.18 (t, J = 1.2 Hz, 1H), 7.09
(s, 1H), 7.04 (dd, J = 5.1, 3.7 Hz, 1H); 13C NMR (125 MHz, CDCl3) 140.4,
133.7, 129.6, 128.8, 127.5, 122.0, 121.0, 81.6, 64.5; MS (ESI) m/z 174.9 ([M
H]); HRMS (EI) calcd for C12H10N2 (M) 174.0252, found 174.0257.
1-(Tridec-1-ynyl)-1H-imidazole (3j). yellow oil; 1H NMR (500
MHz, CDCl3) 7.68 (s, 1H), 7.07 (s, 1H), 7.01 (s, 1H), 2.36 (t, J = 7.1
Hz, 2H), 1.57 (dd, J = 14.9, 7.3 Hz, 2H), 1.48 1.37 (m, 2H), 1.28 (d,
J = 14.4 Hz, 14H), 0.88 (t, J = 6.9 Hz, 3H); 13C NMR (125 MHz,
CDCl3) 140.2, 128.9, 122.0, 70.8, 70.0, 32.1, 29.8, 29.7, 29.5, 29.3,
29.1, 28.6, 22.9, 18.3, 14.3; MS (ESI) m/z 247.1 ([M H]); HRMS
(EI) calcd for C16H26N2 (M) 246.2096, found 246.2102.
1-(Phenylethynyl)-1H-benzo[d]imidazole (5a):8,16a yellow
oil; 1H NMR (500 MHz, CDCl3) 8.17 (s, 1H), 7.85 (d, J = 7.9 Hz,
1H), 7.67 (d, J = 7.9 Hz, 1H), 7.62 7.55 (m, 2H), 7.48 7.36 (m, 5H);
13
C NMR (125 MHz, CDCl3) 143.9, 142.2, 134.8, 134.1, 132.0, 131.5,
129.2, 128.84, 128.8, 125.0, 124.3, 121.6, 121.1, 111.2, 76.7, 73.8; MS
(ESI) m/z 218.8 ([M H]).
1-(p-Tolylethynyl)-1H-benzo[d]imidazole (5b): yellow solid;
mp 7476 C; 1H NMR (500 MHz, CDCl3) 8.15 (s, 1H), 7.84
(d, J = 7.9 Hz, 1H), 7.66 (d, J = 7.9 Hz, 1H), 7.47 (d, J = 8.1 Hz, 2H),
7.45 7.35 (m, 2H), 7.21 (d, J = 7.9 Hz, 2H), 2.40 (s, 3H); 13C NMR
(125 MHz, CDCl3) 143.9, 142.2, 139.6, 134.8, 132.0, 129.6, 125.0, 124.2,
121.0, 118.4, 111.3, 76.1, 73.8, 21.8; MS (ESI) m/z 232.8 ([M H]);
HRMS (EI) calcd for C16H12N2 (M) 232.1000, found 232.1002.
1-((4-Chlorophenyl)ethynyl)-1H-benzo[d]imidazole (5c):
white solid; mp 8890 C; 1H NMR (400 MHz, CDCl3) 8.13 (s,
1H), 7.83 (d, J = 7.8 Hz, 1H), 7.63 (d, J = 7.9 Hz, 1H), 7.50 (d, J = 8.5 Hz,
2H), 7.467.33 (m, 4H); 13C NMR (125 MHz, CDCl3) 143.7, 142.2,
135.4, 134.7, 133.2, 129.2, 125.1, 124.4, 121.2, 120.1, 111.2, 77.5, 72.8;
MS (ESI) m/z 253.1 ([M H]); HRMS (EI) calcd for C15H9ClN2
(M) 252.0454, found 252.0456.
1-((3-Bromophenyl)ethynyl)-1H-benzo[d]imidazole (5d):
white solid; mp 5052 C; 1H NMR (500 MHz, CDCl3) 8.15 (s, 1H),
7.85 (d, J = 8.0 Hz, 1H), 7.73 (s, 1H), 7.65 (d, J = 7.9 Hz, 1H), 7.52 (dd, J =
15.8, 7.8 Hz, 2H), 7.42 (dt, J = 25.6, 7.4 Hz, 2H), 7.28 (d, J = 7.9 Hz, 1H); 13C
E
NOTE
NMR (125 MHz, CDCl3) 143.7, 142.2, 134.6, 132.3, 130.4, 130.3, 125.2,
124.5, 123.6, 122.6, 121.1, 111.2, 77.8, 72.5; MS (ESI) m/z 296.9 ([M
H]); HRMS (EI) calcd for C15H9BrN2 (M), 295.9949, found 295.9940.
4-((1H-Benzo[d]imidazol-1-yl)ethynyl)benzonitrile
2-Ethyl-1-((4-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole (5n): yellow oil; 1H NMR (500 MHz, CDCl3) 7.61 (q, J = 8.4
Hz, 4H), 7.12 (d, J = 1.4 Hz, 1H), 6.95 (d, J = 1.4 Hz, 1H), 2.92 (q, J = 7.6
Hz, 2H), 1.41 (t, J = 7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) 153.8,
131.8, 130.8, 130.6, 128.3, 125.73, 125.7, 125.1, 122.9, 121.4, 80.4, 71.9,
21.0, 11.8; MS (ESI) m/z 265.0 ([M H]); HRMS (EI) calcd for
C14H11F3N2 (M) 264.0874, found 264.0873.
(5e):
1-((4-Chlorophenyl)ethynyl)-2-isopropyl-1H-imidazole
(5o): yellow oil; 1H NMR (500 MHz, CDCl3) 7.467.41 (m, 2H),
7.387.34 (m, 2H), 7.09 (d, J = 1.4 Hz, 1H), 6.95 (d, J = 1.4 Hz, 1H),
3.32 (dt, J = 13.8, 6.9 Hz, 1H), 1.41 (d, J = 6.9 Hz, 6H); 13C NMR (125
MHz, CDCl3) 157.2, 135.1, 132.9, 129.1, 127.9, 121.3, 120.2, 79.1,
72.0, 27.3, 21.0; MS (ESI) m/z 245.1 ([M H]); HRMS (EI) calcd
for C14H13ClN2 (M) 244.0767, found 244.0766.
1-((3-Bromophenyl)ethynyl)-2-isopropyl-1H-imidazole
(5p): yellow oil; 1H NMR (500 MHz, CDCl3) 7.65 (t, J = 1.6 Hz, 1H),
7.52 (ddd, J = 8.0, 1.8, 0.9 Hz, 1H), 7.47 7.41 (m, 1H), 7.26 (dd, J =
15.6, 7.7 Hz, 1H), 7.09 (d, J = 1.5 Hz, 1H), 6.95 (d, J = 1.4 Hz, 1H), 3.32
(dt, J = 13.8, 6.9 Hz, 1H), 1.42 (d, J = 6.9 Hz, 6H); 13C NMR (125 MHz,
CDCl3) 157.2, 134.3, 132.1, 130.2, 128.0, 123.7, 122.6, 121.3, 79.4,
71.7, 27.3, 21.1; MS (ESI) m/z 289.1 ([M H]); HRMS (EI) calcd
for C14H13BrN2 (M) 288.0262, found 288.0268.
1-((3-Bromophenyl)ethynyl)-2-methyl-1H-imidazole (5h):
yellow oil; 1H NMR (500 MHz, CDCl3) 7.65 (t, J = 1.7 Hz, 1H), 7.51
(ddd, J = 8.1, 1.8, 1.0 Hz, 1H), 7.42 (dt, J = 7.6, 1.1 Hz, 1H), 7.25 (dd,
J = 14.8, 6.9 Hz, 1H), 7.09 (d, J = 1.5 Hz, 1H), 6.92 (d, J = 1.5 Hz, 1H), 2.55 (s,
3H); 13C NMR (125 MHz, CDCl3) 149.1, 134.4, 132.2, 130.3, 130.2, 128.2,
123.6, 122.6, 121.4, 79.4, 71.5, 13.5; MS (ESI) m/z 261.1 ([M H]);
HRMS (EI) calcd for C12H9BrN2 (M) 259.9949, found 259.9951.
CDCl3) 7.61 (dd, J = 19.3, 8.3 Hz, 4H), 7.11 (d, J = 1.2 Hz, 1H),
6.95 (d, J = 1.1 Hz, 1H), 3.33 (dt, J = 13.8, 6.9 Hz, 1H), 1.41 (d, J = 6.9
Hz, 6H); 13C NMR (125 MHz, CDCl3) 157.3, 131.8, 130.8, 130.6,
128.1, 125.74, 125.7, 125.1, 122.9, 121.3, 80.4, 72.1, 27.4, 21.1; MS
(ESI) m/z 279.1 ([M H]); HRMS (EI) calcd for C15H13F3N2
(M) 278.1031, found 278.1028.
2-Methyl-1-(phenylethynyl)-1H-benzo[d]imidazole (5i):
yellow oil; 1H NMR (500 MHz, CDCl3) 7.70 (dd, J = 6.7, 2.0 Hz, 1H),
7.63 7.51 (m, 3H), 7.44 7.37 (m, 3H), 7.37 7.29 (m, 2H), 2.76 (s,
3H); 13C NMR (125 MHz, CDCl3) 153.6, 141.9, 135.7, 132.0, 129.1,
128.8, 124.1, 124.0, 121.8, 119.8, 110.9, 76.5, 76.0, 14.4; MS (ESI) m/z
233.1 ([M H]); HRMS (EI) calcd for C16H12N2 (M) 232.1000,
found 232.0998.
1-((3-Bromophenyl)ethynyl)-2-propyl-1H-imidazole (5r):
yellow oil; 1H NMR (500 MHz, CDCl3) 7.63 (t, J = 1.6 Hz, 1H), 7.53
7.46 (m, 1H), 7.41 (dd, J = 7.7, 1.1 Hz, 1H), 7.23 (t, J = 7.9 Hz, 1H),
7.08 (d, J = 1.5 Hz, 1H), 6.94 (d, J = 1.4 Hz, 1H), 2.84 (t, J = 7.5 Hz, 2H),
1.85 (dd, J = 14.9, 7.4 Hz, 2H), 1.02 (t, J = 7.4 Hz, 3H); 13C NMR (125
MHz, CDCl3) 152.7, 134.3, 132.1, 130.21, 130.2, 128.2, 123.7, 122.5,
121.3, 79.4, 71.5, 29.3, 21.2, 14.0; MS (ESI) m/z 289.1 ([M H]);
HRMS (EI) calcd for C14H13BrN2 (M) 288.0262, found 288.0264.
1-((4-Chlorophenyl)ethynyl)-2-methyl-1H-benzo[d]imidazole (5j): yellow oil; 1H NMR (500 MHz, CDCl3) 7.70 (dd, J =
6.4, 2.4 Hz, 1H), 7.577.47 (m, 3H), 7.417.36 (m, 2H), 7.367.29
(m, 2H), 2.75 (s, 3H); 13C NMR (125 MHz, CDCl3) 153.5, 142.0,
135.6, 135.2, 133.1, 129.2, 124.2, 124.0, 120.3, 119.9, 110.8, 77.4, 75.0,
14.4; MS (ESI) m/z 267.1 ([M H]); HRMS (EI) calcd for
C16H11ClN2 (M) 266.0611, found 266.0608.
2-Ethyl-1-(p-tolylethynyl)-1H-imidazole (5k): yellow oil; 1H
NMR (500 MHz, CDCl3) 7.39 (d, J = 8.1 Hz, 2H), 7.17 (d, J = 8.0 Hz,
2H), 7.08 (d, J = 1.4 Hz, 1H), 6.92 (d, J = 1.4 Hz, 1H), 2.89 (q, J = 7.6 Hz,
2H), 2.37 (s, 3H), 1.39 (t, J = 7.6 Hz, 3H); 13C NMR (125 MHz,
CDCl3) 153.7, 139.3, 131.7, 129.5, 127.8, 121.4, 118.5, 77.6, 72.9, 21.7,
20.9, 11.8; MS (ESI) m/z 211.3 ([M H]); HRMS (EI) calcd for
C14H14N2 (M) 210.1157, found 210.1159.
2-Propyl-1-((4-(trifluoromethyl)phenyl)ethynyl)-1H-imidazole (5s): yellow oil; 1H NMR (500 MHz, CDCl3) 7.62 (dd, J =
20.9, 8.1 Hz, 4H), 7.12 (s, 1H), 6.96 (s, 1H), 2.87 (t, J = 7.5 Hz, 2H), 1.87
(dd, J = 14.8, 7.4 Hz, 2H), 1.03 (t, J = 7.4 Hz, 3H); 13C NMR (125 MHz,
CDCl3) 152.8, 131.8, 128.3, 125.7, 121.3, 80.5, 71.9, 29.4, 21.3, 14.0;
MS (ESI) m/z 279.1 ([M H]); HRMS (EI) calcd for C15H13F3N2
(M) 278.1031, found 278.1027.
4-Methyl-1-(phenylethynyl)-1H-imidazole (5ta):8b yellow
solid; mp 7577 C; tR = 10.3; 1H NMR (500 MHz, CDCl3) 7.72
(s, 1H), 7.54 7.45 (m, 2H), 7.40 7.32 (m, 3H), 6.89 (s, 1H), 2.25 (s,
3H); 13C NMR (125 MHz, CDCl3) 139.7, 138.7, 131.9, 129.1, 128.8,
121.6, 118.0, 78.6, 70.0, 13.7; MS (ESI) m/z 183.2 ([M H]).
5-Methyl-1-(phenylethynyl)-1H-imidazole (5tb):8b yellow
oil; tR = 10.4; 1H NMR (500 MHz, CDCl3) 7.75 (s, 1H), 7.51 (dd,
J = 6.5, 3.0 Hz, 2H), 7.41 7.35 (m, 3H), 6.79 (s, 1H), 2.35 (s, 3H); 13C
NMR (125 MHz, CDCl3) 139.2, 131.9, 130.6, 129.1, 128.8, 126.1,
121.5, 77.0, 73.1, 9.4; MS (ESI) m/z 182.9 ([M H]).
1-(Tridec-1-ynyl)-1H-benzo[d]imidazole (5u): yellow oil; 1H
NMR (500 MHz, CDCl3) 8.05 (s, 1H), 7.81 (d, J = 7.9 Hz, 1H),
7.57 (d, J = 8.0 Hz, 1H), 7.36 (ddd, J = 16.3, 11.3, 4.1 Hz, 2H), 2.48
(t, J = 7.1 Hz, 2H), 1.70 1.60 (m, 2H), 1.48 (dd, J = 15.0, 7.2 Hz, 2H),
1.40 1.16 (m, 14H), 0.88 (t, J = 6.9 Hz, 3H); 13C NMR (125 MHz,
CDCl3) 144.2, 124.7, 123.9, 120.9, 111.1, 74.0, 68.3, 33.8, 32.2,
29.9, 29.8, 29.6, 29.4, 29.2, 28.9, 22.9, 18.6, 14.4; MS (ESI) m/z 297.1
([M H]); HRMS (EI) calcd for C20H28N2 (M) 296.2252, found
296.2256.
1-((4-Chlorophenyl)ethynyl)-2-ethyl-1H-imidazole (5l):
yellow oil; 1H NMR (500 MHz, CDCl3) 7.477.39 (m, 2H),
7.387.33 (m, 2H), 7.09 (d, J = 1.5 Hz, 1H), 6.94 (d, J = 1.5 Hz,
1H), 2.90 (q, J = 7.6 Hz, 2H), 1.39 (t, J = 7.6 Hz, 3H); 13C NMR (125
MHz, CDCl3) 153.7, 135.2, 133.0, 129.1, 128.1, 121.4, 120.1, 79.1,
71.9, 21.0, 11.9; MS (ESI) m/z 231.1 ([M H]); HRMS (EI) calcd
for C13H11ClN2 (M) 230.0611, found 230.0611.
1-((3-Bromophenyl)ethynyl)-2-ethyl-1H-imidazole (5m):
yellow oil; 1H NMR (500 MHz, CDCl3) 7.64 (t, J = 1.6 Hz, 1H), 7.50
(ddd, J = 8.0, 1.8, 1.0 Hz, 1H), 7.45 7.39 (m, 1H), 7.25 (dd, J = 15.9,
8.0 Hz, 1H), 7.09 (d, J = 1.5 Hz, 1H), 6.94 (d, J = 1.4 Hz, 1H), 2.90 (q, J =
7.6 Hz, 2H), 1.40 (t, J = 7.6 Hz, 3H); 13C NMR (125 MHz, CDCl3)
153.7, 134.4, 132.1, 130.22, 130.2, 128.2, 123.7, 122.5, 121.3, 79.3, 71.5,
21.0, 11.8; MS (ESI) m/z 275.1 ([M H]); HRMS (EI) calcd for
C13H11BrN2 (M) 274.0106, found 274.0109.
F
NOTE
ASSOCIATED CONTENT
bS
130, 1820. (d) Raw, S. A.; Reid, M.; Roman, E.; Taylor, R. J. K. Synlett
2004, 819.
(15) See the Supporting Information for details.
(16) (a) Laroche, C.; Kerwin, S. M. J. Org. Chem. 2009, 74, 9229.
(b) Laroche, C.; Kerwin, S. M. Tetrahedron Lett. 2009, 50, 5194.
AUTHOR INFORMATION
Corresponding Author
*E-mail: shangzc@zju.edu.cn.
REFERENCES
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H. Y.; Lohse, A. G.; Hayashi, R.; Lu, Z. J.; Zhang, Y.; Hsung, R. P. Chem.
Rev. 2010, 110, 5064. (b) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int.
Ed. 2010, 49, 2840. (c) Tracey, M. R.; Hsung, R. P.; Antoline, J.; Kurtz,
K. C. M.; Shen, L.; Slafer, B. W.; Zhang, Y. Sci. Synth. 2005, 21, 404.
(d) Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
(e) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
(2) (a) Ishihara, T.; Mantani, T.; Konno, T.; Yamanaka, H. Tetrahedron
2006, 62, 3783. (b) Xu, Z. Q.; Joshi, R. V.; Zemlicka, J. Tetrahedron 1995,
51, 67.
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