2006
DOI: 10.1016/j.tetlet.2005.10.147
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An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives

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Cited by 7 publications
(6 citation statements)
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“…To a solution of 1,2-diiodo-4,5-dimethoxy-3-methylbenzene (2.0 g, 4.95 mmol) in 120 mL of a mixture of THF and Et 2 O (1:1) was added dropwise at −78 °C isopropylmagnesium chloride (2 M in THF, 2.72 mL, 5.44 mmol). After the mixture was stirred for 2 h at that temperature, B(O i -Pr) 3 (10.50 mL, 14.84 mmol) was added.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…To a solution of 1,2-diiodo-4,5-dimethoxy-3-methylbenzene (2.0 g, 4.95 mmol) in 120 mL of a mixture of THF and Et 2 O (1:1) was added dropwise at −78 °C isopropylmagnesium chloride (2 M in THF, 2.72 mL, 5.44 mmol). After the mixture was stirred for 2 h at that temperature, B(O i -Pr) 3 (10.50 mL, 14.84 mmol) was added.…”
Section: Methodsmentioning
confidence: 99%
“…To the concentrated sample, hexane was added, and the resulting precipitate was isolated to give 1.05 g of the pure product as a white solid in 67% yield: mp >163 °C (decomposition); IR (Microscope, cm −1 ) 2959, 1585, 1506, 1373, 1310, 1263, 1199; 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.14 (s, 2H), 7.17 (s, 1H), 6.80 (s, 1H), 3.69 (s, 3H), 3.68 (s, 3H); 13 Preparation of 2-Iodo-3-methyl-4,5-dimethoxyphenylboronic acid 4e. To a solution of 1,2-diiodo-4,5-dimethoxy-3methylbenzene 65 (2.0 g, 4.95 mmol) in 120 mL of a mixture of THF and Et 2 O (1:1) was added dropwise at −78 °C isopropylmagnesium chloride (2 M in THF, 2.72 mL, 5.44 mmol). After the mixture was stirred for 2 h at that temperature, B(Oi-Pr) 3 (10.50 mL, 14.84 mmol) was added.…”
mentioning
confidence: 99%
“…In addition, the Sonogashira coupling has been employed recently for the connection of an iodinated pyrimidinone to 34-or 36-crown-10 for the selective self-assembly of some hydrogen-bonded heterotrimers, 501 and for the alkynylation of dibenzo-24-crown-8 ethers for complexation studies. 502 Other recent examples of the Sonogashira reaction applied to the preparation of arylene-acetylene macrocycles containing substructures such as copper-cyclobutadiene complexes, 503 cyclopentadienes, 504 allenes, 505 and enediynes 506 can also be found. An example of the latter type is the synthesis of multicyclic cagelike cyclobutene-containing structure 340, which has been prepared after Sonogashira cross-coupling reaction of diethynylpropellane derivative 334 with diethyl-(4-iodophenyl)triazene (335) (Scheme 97).…”
Section: Synthesis Of Molecules For Nanostructuresmentioning
confidence: 99%
“…Other recent illustrative examples of the application of the palladium−copper promoted cross-coupling alkynylation reaction to the synthesis of related phenylene−acetylene macrocycles, the asymmetric synthesis of macrocyclic binaphthol dimers,500a and the synthesis of phenylenebis(ethynyl)-tethered bis-BINOL ligands 500b can be found. In addition, the Sonogashira coupling has been employed recently for the connection of an iodinated pyrimidinone to 34- or 36-crown-10 for the selective self-assembly of some hydrogen-bonded heterotrimers, and for the alkynylation of dibenzo-24-crown-8 ethers for complexation studies 96
97
…”
Section: 9 Synthesis Of Molecules For Nanostructuresmentioning
confidence: 99%
“…Coupling of 7 with 4-bromocatechol was templated with Cs + and 4-bromo-DB24C8 (8) was obtained in good yield (Scheme 3). 31 Halogen-metal exchange of 8 with i-propyl magnesium chloride or i-propyl magnesium chloride?LiCl at 0 uC 32 did not take place and although improved solubility of 8 (cf. 1) at 278 uC enabled us to carry out bromine-lithium exchange of 8, subsequent transmetalation to zinc was incomplete 33 and emphasises the requirement for magnesium-zinc transmetalation.…”
Section: Entrymentioning
confidence: 99%