À
C X (X=Br, I) Bond-Tolerant Aerobic Oxidative Cross-Coupling
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actions between nucleophiles and allylic alcohols, there
are only two example in existence, which require toxic
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an important complementary method to prepare the
aryl halide-containing compounds, which are still elu-
sive via traditional coupling protocols.
Experimental Section
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Typical Procedure
4-Iodophenylboronic acid (124.0 mg, 0.5 mmol), PdACTHNUTRGNEUNG(OAc)2
(2.8 mg, 0.0125 mmol), and CuCl (2.5 mg, 0.025 mmol) were
combined in a dry Schlenk tube containing 1.5 mL dry sol-
vent (DMSO/HOAc=1/1, v/v). 1.2 equivalents of 1-penten-
3-ol (60 mL, 0.6 mmol) were then added at room tempera-
ture. Subsequently, the tube was purged with a balloon pres-
sure of oxygen for 3 times. The reaction mixture was stirred
at 508C for 20 h. After the reaction was stopped, the solu-
tion was diluted with 5 mL saturated NaCl solution. The
mixture was extracted with Et2O (150 mL), washed with sa-
turated NaHCO3 (3ꢂ10 mL), saturated NaCl (2ꢂ10 mL)
and dried over Na2SO4. The solvent was removed, and the
residue was subjected to flash column chromatography with
petroleum/Et2O (100/1) as eluent to obtain the desired prod-
uct 1-(4-iodophenyl)pentan-3-one; yield: 115.8 mg (80%).
Acknowledgements
We thank the generous support from the National Natural
Science Foundation of China (20702040, 20832003,
20972118).
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