Palladium-Catalyzed Novel Arylations
of Cyclic β-Bromo α,β-Unsaturated Aldehydes
with Triarylbismuths as Multicoupling Organometallic Nucleo­philes

Maddali L. N. Rao; Debasis Banerjee; Ritesh J. Dhanorkar

doi:10.1055/s-0030-1259290

LETTER

Palladium-Catalyzed Novel Arylations of Cyclic β-Bromo α,β-Unsaturated Aldehydes with Triarylbismuths as Multicoupling Organometallic Nucleophiles

Maddali L. N. Rao*, Debasis Banerjee, Ritesh J. Dhanorkar
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India
Fax: +91(512)2597532; e-Mail: maddali@iitk.ac.in;

Abstract

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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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References and Notes

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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), K₃PO₄ (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 H₂O (10 mL) and the mixture was extracted with EtOAc (3 × 15 mL). The combined organic extracts were washed with H₂O (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 ^¹H NMR, ^¹³C NMR, IR spectroscopic data and HRMS (ESI).

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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Zusatzmaterial

Supporting Information

Palladium-Catalyzed Novel Arylations of Cyclic β-Bromo α,β-Unsaturated Aldehydes with Triarylbismuths as Multicoupling Organometallic Nucleo­philes

Palladium-Catalyzed Novel Arylations of Cyclic β-Bromo α,β-Unsaturated Aldehydes with Triarylbismuths as Multicoupling Organometallic Nucleophiles