Abstract
Cross-coupling arylations of cyclic β-bromo α,β -unsaturated
aldehydes were carried out with triarylbismuths as atom-efficient
multicoupling organometallic reagents under palladium-catalyzed
conditions. These reactions afforded the corresponding arylated
alkenes in an efficient manner with good to high yields.
Key words
palladium catalysis - cyclic β-bromo α,β -unsaturated aldehyde - cross-coupling - triarylbismuths - tetrasubstituted
alkenes
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Representative
Procedure : An oven-dried Schlenk tube under a nitrogen atmosphere
was charged with 1-bromo-3,4-dihydronaphthalene-2-carbaldehyde (0.825
mmol, 0.196 g) followed by triphenylbismuth (0.25 mmol, 0.11 g),
K3 PO4 (0.50 mmol, 0.106 g), PdCl2 (PPh3 )2 (0.0225
mmol, 0.0158 g) and anhyd DMF (3 mL). The reaction mixture was stirred in
an oil bath at 90 ˚C for 1 h. Then the contents were cooled to
r.t. and the reaction was quenched with H2 O (10 mL) and the
mixture was extracted with EtOAc (3 × 15 mL). The combined
organic extracts were washed with H2 O (2 × 10 mL),
brine (10 mL), dried over anhyd MgSO4 and concentrated.
The crude product mixture thus obtained was purified by silica gel
column chromatography using 1% EtOAc-petroleum
ether as eluent to obtain 1-phenyl-3,4-dihydronaphthale-2-carbaldehyde(2a ) as a pale yellow solid (0.169 g, 96%).
All the products were characterized by ¹ H NMR, ¹³ C
NMR, IR spectroscopic data and HRMS (ESI).
10 In all the coupling reactions, 0.3
equiv of bromoaldehydes was employed in excess. However, the product
yields were calculated based on the three couplings from triaryl-bismuths.
Thus, 0.75 mmol of the cross-coupled product corresponds to 100% yield.
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