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DOI: 10.1055/s-2005-865283
Stereoselective Synthesis of (E)-β-Arylvinyl Bromides by Microwave-Induced Hunsdiecker-Type Reaction
Publikationsverlauf
Publikationsdatum:
23. März 2005 (online)
Abstract
(E)-β-Arylvinyl bromides were readily prepared in a short reaction time (1-2 min) by microwave irradiation of the corresponding 3-arylpropenoic acids in the presence of N-bromosuccinimide and a catalytic amount of lithium acetate. Furthermore, two facile strategies for the efficient synthesis of (E)-β-bromo-4-arylethynylstyrene and (E)-β-bromo-4-arylstyrene have been developed by respectively combining Sonogashira and Suzuki coupling reaction with Hunsdiecker-type reaction. Formation of cis-α-bromo-β-lactone by microwave irradiation of cis-cinnamic acid with NBS provides a useful support for the mechanistic study of the present halodecarboxylation reaction.
Key words
(E)-β-arylvinyl bromides - α,β-unsaturated carboxylic acids - stereoselective synthesis - microwave irradiation - Hunsdiecker-type reaction
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Microwave irradiation of 4-phenylbut-3-enoic acid (162 mg, 1 mmol) in MeCN-H2O (4.6 mL:0.4 mL) solvent containing NBS (187 mg, 1.05 mmol) and catalytic amount of LiOAc (13 mg, 0.2 mmol) for 1 min gave the corresponding trans-3-bromo-4-phenylbutenolide in 85% yield. The physical data of trans-3-bromo-4-phenylbutenolide are as follows: colorless oil; IR (Nujol): 1810 cm-1 (γ-lactone C=O); 1H NMR (270 MHz, CDCl3): δ = 2.96 (1 H, dd, J = 18.1, 6.6 Hz), 3.23 (1 H, dd, J = 18.1, 7.6 Hz), 4.24 (1 H, m, J = 6.6, 7.6 Hz), 5.64 (1 H, d, J = 5.3 Hz), 7.35-7.44 (5 H, m); 13C NMR (67.5 MHz, CDCl3): δ = 38.73, 45.63, 87.75, 125.46, 128.97, 129.29, 135.74, 172.99; EIMS: m/z (%) = 242 [(M + 2)+, 24], 240 (M+, 25), 161 (45), 107 (100); HRMS: m/z calcd for C10H9 79BrO2 [M+]: 239.9785; found: 239.9762.
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cis-3-Bromo-4-phenyloxetan-2-one (4) was prepared from cis-cinnamic acid in 85% yield according to the general procedure. The physical data of 4 are as follows: colorless oil; IR (neat): 1844 cm-1 (β-lactone C=O); 1H NMR (270 MHz, CDCl3): δ = 5.58 (1 H, d, J = 5.94 Hz), 5.74 (1 H, d, J = 5.94 Hz), 7.36-7.45 (5 H, m); EIMS: m/z (%) = 228 [(M + 2)+, 24], 226 (M+, 25), 182 (M+ - CO2, 100); HRMS: m/z calcd for C9H7 79BrO2 [M+]: 225.9629; found: 225.9627.