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16 When 1a was
subjected to the reaction conditions reported in Table
[¹ 2 no
reduction product 4 was formed suggesting
that the reduction of 1a to 4 proceeds through
a palladium-catalyzed process.
17
Typical Procedure
for the Palladium-Catalyzed Hydro-arylation of Norbornene Derivatives
with Arenediazo-nium Tetrafluoroborates - Hydroarylation
of 1a with 2a (Table 2, entry 1)
1a (105.1 mg, 0.50 mmol) and Pd(OAc)2 (5.6
mg, 0.025 mmol) in anhyd THF (4.0 mL), 2a (233.8
mg, 1.0 mmol) was added at r.t. under argon. The reaction mixture
was cooled in an ice bath. Then, i -Pr3 SiH (205 µL,
1.0 mmol) was added and the reaction mixture was stirred at 15 ˚C
for 40 min under argon (the reactor was protected from light with
aluminum film). After this time, the mixture was diluted with EtOAc,
washed with H2 O, dried over Na2 SO4 ,
and concentrated under reduced pressure. The residue was purified
by chromatography on silica gel [n -hexane-EtOAc,
90:10 (v/v)] to afford 120.8 mg (73% yield)
of 3a , mp 64-66 ˚C.
IR (KBr): 2968, 1735, 1198 cm-¹ . ¹ H
NMR (400 MHz, CDCl3 ): δ = 7.89 (d, J = 8.2 Hz, 2
H), 7.38 (d, J = 8.2
Hz, 2 H), 3.70 (s, 6 H), 3.64 (t, J = 7.4 Hz,
1 H), 3.19 (ddd, J
1 = 11.7
Hz, J
2 = 4.5
Hz, J
3 = 1.4
Hz, 1 H), 2.99 (dd, J
1 = 11.8
Hz, J
2 = 3.7
Hz, 1 H), 2.75-270 (m, 1 H), 2.73-2.58 (m, 1 H),
2.13 (ddd, J
1 = 11.1
Hz, J
2 = 8.8
Hz, J
3 = 3.7
Hz, 1 H), 1.74-1.65 (m, 2 H), 1.42-1.26 (m, 1
H). ¹³ C NMR (100.6 MHz, CDCl3 ): δ = 197.9,
172.9, 172.6, 151.9, 134.9, 128.5, 127.5, 51.7, 51.5, 47.7, 46.2,
45.9, 41.6, 40.2, 37.5, 33.2, 26.6. MS: m/z (relative
intensity) = 330 (12) [M+ ],
298 (10), 270 (57), 185 (232), 43 (100).
18 NOESY experiments on 3a :
for selected H-H interactions, see Figure
[²
Figure 2
19 Doyle MP.
Bryker WJ.
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20
Palladium-Catalyzed
Hydroarylation of 1a with 2a Generated In Situ
3 ˙OEt2 (140 µL, 1.1
mmol) in anhyd THF (1 mL) was cooled at -15 ˚C
and p -aminoacetophenone (135.1 mg, 1
mmol) was added. Then, tert -butyl nitrite
(160 µL, 1.3 mmol) in 1 mL of the same solvent was added
dropwise to the rapidly stirred reaction solution over a period
of 10 min. Following complete addition, the temperature of the solution was
maintained at -15 ˚C for 10 min and subsequently allowed
to warm to 5 ˚C in an ice-water bath over a period of
20 min. Then, the reaction mixture was warmed to r.t. and stirred
at the same temperature till the starting p -amino-acetophenone
was converted into p -acetylbenzenediazo-nium
tetrafluoroborate. The reaction mixture was cooled in an ice bath
and 1a (105.1 mg, 0.50 mmol), Pd(OAc)2 (5.6 mg,
0.025 mmol), i -Pr3 SiH (205 µL,
1.0 mmol), and of anhyd THF (2 mL) were added. The reaction mixture
was allowed to warm to 20 ˚C and stirred at that
temperature for 6 h under argon (the reactor was protected from
light with aluminum film). After this time, the mixture was diluted with
EtOAc, washed with H2 O, dried over Na2 SO4 ,
and concentrated under reduced pressure. The residue was purified
by chromatography on silica gel [n -hexane-EtOAc, 90:10
(v/v)] to afford 106.3 mg (64% yield)
of 3a .
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