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1.64 ppm (s, 3H, CH3); 13C{1H} NMR (126 MHz, CDCl3): d=212.50
(C=O), 191.31 (C carbene), 139.47 (CH aromatic IMes), 134.92 (CH
aromatic IMes), 129.34 (CH aromatic IMes), 41.13 (CH2), 29.44 (CH3),
21.26 (CH3 p-phenyl IMes), 17.99 ppm (CH3 aromatic IMes); FTIR
(ATR): u˜ =1643 cmÀ1 (C=O); elemental analysis calcd (%) for
C24H29AuN2O, 558.48 gmolÀ1: C 51.60, H 5.16, N 5.16; found: C
51.62, H 5.23, N 5.02.
Preparation of [Au(NHC)(CH2COCH3)] (2a–g), route B
(Scheme 3)
A mixture of [Au(NHC)(Cl)] (1 equiv) and K2CO3 (6 equiv) in acetone
(2 mL) was stirred at 608C for 24–72 h. The solution was then fil-
tered through a pad of Celite, the solvent was removed under
vacuum. The resulting solid was dissolved in the minimum amount
of CH2Cl2 (2–3 mL) and precipitated by addition of n-pentane (ca.
10 mL). The precipitate was collected by filtration, washed with n-
pentane (35 mL), and dried under vacuum, affording the corre-
sponding [Au(NHC)(CH2COCH3)] as a microcrystalline white solid.
[Au(SIPr)(CH2COCH3)] 1,3-bis(2,6-di-iso-propylphenyl)imid-
azolidin-2-yl)(2-oxopropyl)gold (2c)
Complex 2c was synthesized following route B by using [Au-
(SIPr)(Cl)] (100 mg, 0.16 mmol, 1 equiv) and K2CO3 (138.88 mg,
3.52 mmol, 6 equiv) in acetone (2 mL). The reaction was stirred for
72 h at 608C. The desired product was obtained as a white solid in
Preparation of [Au(IPr)(CH2COCH3)] (2a), route C (Scheme 3)
[Au(IPr)(OH)] (400 mg, 0.66 mmol, 1 equiv) was dissolved in ace-
tone (5 mL) and stirred for 4 h at room temperature. The solvent
was then removed under vacuum. The resulting solid was dis-
solved in the minimum amount of CH2Cl2 (2–3 mL) and precipitat-
ed by addition of n-pentane (ca. 10 mL). The precipitate was col-
lected by filtration, washed with n-pentane (35 mL), and dried
under vacuum, affording the corresponding [Au(IPr)(CH2COCH3)] as
a microcrystalline white solid in 90% yield.
1
97% yield (100 mg, 0.156 mmol). H NMR (300 MHz,CDCl3) d=7.40
(dd, J=8.3 Hz, 7.2 Hz, 2H, CH aromatic SIPr), 7.23 (d, J=7.7 Hz, 4H,
CH aromatic SIPr), 4.00 (s, 4H, CH imidazole SIPr), 3.06 (sept, J=
6.9 Hz, 4H, CH(CH3)2), 1.99 (q, J=0.9 Hz, 2H, CH2), 1.44 (d, J=
0.9 Hz, 12H, CH3), 1.39 (d, J=6.8 Hz, 12H, CH(CH3)2), 1.33 ppm (d,
J=7.0 Hz, 12H, CH(CH3)2); 13C{1H} NMR (126 MHz, CDCl3): d=212.39
(C=O), 212.01 (C carbene), 146.83 (CH aromatic SIPr), 134.49 (CH ar-
omatic SIPr), 129.75 (CH aromatic SIPr), 124.50 (CH aromatic SIPr),
53.72 (CH2 imidazole SIPr), 41.00 (CH2), 29.42 (CH(CH3)2), 29.06
(CH3), 25.11 (CH3), 24.25 ppm (CH3); FTIR (ATR): u˜ =1643 cmÀ1 (C=
O); elemental analysis calcd (%) for C30H43AuN2O, 644.65 gmolÀ1: C
55.88, H 6.79, N 4.42; found: C 55.90, H 6.72, N 4.35.
[Au(IPr)(CH2COCH3)] (1,3-bis(2,6-diisopropylphenyl)-2,3-dihy-
dro-1H-imidazol-2-yl)(2-oxopropyl)gold (2a)
Complex 2a was synthesized following route A by using IPr·HCl
(800 mg,
1.82 mmol,
1 equiv),
[Au(SMe2)(Cl)]
(554.37 mg,
1.82 mmol, 1 equiv), K2CO3 (1.51 g, 10.92 mmol, 6 equiv) in acetone
(10 mL). The reaction mixture was stirred for 48 h at 608C. The de-
sired product was obtained as a white solid in 80% yield
(968.52 mg, 1.51 mmol). Complex 2a was also synthesized follow-
ing route B by using [Au(IPr)(Cl)] (200 mg, 1.82 mmol, 1 equiv) and
K2CO3 (1.51 g, 10.92 mmol, 6 equiv) in acetone (5 mL). The reaction
was stirred for 24 h at 608C. The desired product was obtained as
[Au(SIMes)(CH2COCH3)] 1,3-dimesitylimidazolidin-2-yl)(2-oxo-
propyl)gold (2d)
Complex 2d was synthesized following route B by using [Au-
(SIMes)(Cl)] (100 mg, 0.58 mmol, 1 equiv) and K2CO3 (486.51 mg,
3.52 mmol, 6 equiv) in acetone (2 mL). The reaction mixture was
stirred for 72 h at 608C. The desired product was obtained as
a
white solid in 84% yield (173.82 mg, 0.32 mmol). 1H NMR
a
white solid in 73% yield (75.76 mg, 0.13 mmol). 1H NMR
(500 MHz, CDCl3): d=7.49 (t, J=7.8 Hz, 2H, CH aromatic IPr), 7.28
(d, J=7.8 Hz, 4H, CH aromatic IPr), 7.13 (s, 2H, CH imidazole IPr),
2.56 (sept, J=6.9 Hz, 4H, CH(CH3)2), 2.06 (s, 2H, CH2), 1.53 (s, 3H,
CH3), 1.32 (d, J=6.9 Hz, 12H, CH(CH3)2), 1.21 ppm (d, J=6.9 Hz,
12H, CH(CH3)2); 13C{1H} NMR (126 MHz, CDCl3): d=212.12 (C=O),
193.06 (C carbene), 145.83 (CH aromatic IPr), 134.42 (CH aromatic
IPr), 130.47 (CH aromatic IPr), 124.41 (CH aromatic IPr), 124.15 (CH
aromatic IPr), 122.81 (CH imidazole IPr), 40.71 (CH2), 29.54 (CH3),
28.88 (CH(CH3)2), 24.53 (CH(CH3)2), 24.11 ppm (CH(CH3)2); FTIR (ATR):
u<Ü= > =1643 cmÀ1 (C=O); elemental analysis calcd (%) for
C30H41AuN2O, 642.64 gmolÀ1: C 55.98, H 6.58, N 4.35; found: C
55.97, H 6.38, N 4.37.
(400 MHz, CDCl3): d=6.95 (s, 4H, CH aromatic SIMes), 3.92 (s, 4H,
CH2 imidazole SIMes), 2.31 (s, 12H, CH3 aromatic SIMes), 2.29 (s,
6H, CH3 p-phenyl SIMes), 2.02 (d, J=0.8 Hz, 2H, CH2), 1.54 ppm (s,
3H, CH3); 13C{1H} NMR (101 MHz, CDCl3): d=212.49 (C=O), 211.58 (C
carbene), 138.66 (CH aromatic SIMes), 135.81 (CH aromatic SIMes),
135.09 (CH aromatic SIMes), 129.61 (CH aromatic SIMes), 50.86 (CH2
imidazole SIMes), 41.41 (CH2), 29.30 (CH3), 21.18 (CH3 p-phenyl
SIMes), 18.17 ppm (CH3 aromatic SIMes); FTIR (ATR): u˜ =1645 cmÀ1
(C=O); elemental analysis calcd (%) for C24H31AuN2O,
560.49 gmolÀ1: C 51.43, H 5.58, N 5.00; found: C 51.35, H 5.71, N
4.97.
[Au(IPrCl)(CH2COCH3)] 4,5-dichloro-1,3-bis(2,6-di-iso-propyl-
phenyl)-2,3-dihydro-1H-imidazol-2-yl)(2-oxopropyl)gold (2e)
[Au(IMes)(CH2COCH3)] (1,3-dimesityl-2,3-dihydro-1H-imid-
azol-2-yl)(2-oxopropyl)gold (2b)
Complex 2e was synthesized by following route B by using
[Au(IPrCl)(Cl)] (100 mg, 0.145 mmol, 1 equiv) and K2CO3 (120.2 mg,
0.870 mmol, 6 equiv) in acetone (2 mL). The reaction mixture was
stirred for 48 h at 608C. The desired product was obtained as
Complex 2b was synthesized following route A by using IMes·HCl
(800 mg, 2.34 mmol, 1 equiv), [Au(SMe2)(Cl)] (172.8 mg, 0.58 mmol,
1 equiv), and K2CO3 (1.95 g, 3.52 mmol, 6 equiv) in acetone (10 mL).
The reaction was stirred for 72 h at 608C. The desired product was
obtained as a white solid in 68% yield (891.31 mg, 1.59 mmol).
Complex 2b was also synthesized following route B by using [Au-
(IMes)(Cl)] (200 mg, 0.373 mmol, 1 equiv) and K2CO3 (g, 3.52 mmol,
6 equiv) in acetone (2 mL). The reaction was stirred for 72 h at
608C. The desired product was obtained as a white solid in 73%
a
white solid in 81% yield (83.17 mg, 0.117 mmol).1H NMR
(500 MHz, CDCl3): d=7.54 (t, J=7.7 Hz, 2H, CH aromatic IPrCl), 7.31
(d, J=7.8 Hz, 4H, CH aromatic IPrCl), 2.46 (2.45 (sept, J=6.8, 4H,
CH(CH3)2), 2.06 (s, 2H, CH2), 1.52 (s, 3H, CH3), 1.32 (d, J=6.8 Hz,
12H, CH(CH3)2), 1.25 ppm (d, J=6.9 Hz, 12H, CH(CH3)2);
13C{1H} NMR (126 MHz, CDCl3): d=212.13 (C=O), 193.01 (C carbene),
146.29 (CH aromatic IPrCl), 131.37 (CH aromatic IPrCl), 124.47 (CH ar-
omatic IPrCl), 118.87 (CH aromatic IPrCl), 39.85 (CH2), 29.56 (CH3),
29.24 (CH(CH3)2), 24.60 (CH(CH3)2), 23.61 ppm (CH(CH3)2); FTIR (ATR):
1
yield (151.62 mg, 0.27 mmol). H NMR (500 MHz, CDCl3): d=7.04 (s,
2H, CH imidazole IMes), 7.00 (s, 4H, CH aromatic IMes), 2.34 (s, 6H,
CH3 p-phenyl IMes), 2.10 (s, 12H, CH3 IMes), 2.09 (s, 3H, CH2)
Chem. Eur. J. 2015, 21, 5403 – 5412
5410
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