2003
DOI: 10.1016/j.jorganchem.2003.08.041
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Triallyl(aryl)silanes serve as a convenient agent for silicon-based cross-coupling reaction of aryl halides

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Cited by 36 publications
(20 citation statements)
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“…We were able to reproduce the results of Hiyama by cross-coupling phenyltriallylsilane with 4-bromoacetophenone (albeit in 70% cf. 81% yield), 36 but diallylgermane 15b did not couple under either these or the optimized conditions for coupling dichlorogermanes 6b and 7b described above. Moreover, phenltriallylgermane gave 4,4 -diacetylbiphenyl (80%) and just traces of cross-coupled product under the Hiyama conditions.…”
Section: Resultsmentioning
confidence: 93%
“…We were able to reproduce the results of Hiyama by cross-coupling phenyltriallylsilane with 4-bromoacetophenone (albeit in 70% cf. 81% yield), 36 but diallylgermane 15b did not couple under either these or the optimized conditions for coupling dichlorogermanes 6b and 7b described above. Moreover, phenltriallylgermane gave 4,4 -diacetylbiphenyl (80%) and just traces of cross-coupled product under the Hiyama conditions.…”
Section: Resultsmentioning
confidence: 93%
“…The cross-coupling reaction of triallyl(phenyl)silane (1a) with 4-bromochlorobenzene with catalyst systems including PdCl 2 , PCy 3 , and TBAF · 3 H 2 O in DMSO-H 2 O afforded the corresponding biaryls without affecting the chloro group in 98% yield. [27] Subsequent cross-coupling with triallyl(4-methoxyphenyl)silane (1c) gave 4-methoxy-p-terphenyl (12) in 87% yield as shown in Scheme 2. Similarly, 4-methyl-m-terphenyl (14) was prepared via identical reaction sequences with 3-bromochlorobenzene in good yields (Scheme 2).…”
Section: Sequential Cross-coupling Reactions Of Bromochlorobenzenesmentioning
confidence: 99%
“…Herein, we present a detailed account of our efforts in the cross-coupling of an array of triallyl(aryl)silanes with a variety of aryl bromides and chlorides. [27,28] Also described are the efficiency of the reaction depending on the number of allyl groups in the arylsilane and its application to unsymmetrical terphenyl synthesis.…”
Section: Introductionmentioning
confidence: 99%
“…21-7.16 (m, 2H), 7.09-7.04 (m, 2H), 4.08 (d, J = 8.9 Hz, 2H), 2.78-2.63 (overlapping region, 16H), 1.81 (septet, J = 6.7 Hz, 2H), 0.93 (d, J = 6.7 Hz, 6H), 0.91 (d, J = 6.5 Hz, 6H). 13 mmol) of isobutyraldehyde through a dropping funnel over 20 minutes. The mixtrure was allowed to stir for 3 h after which 200 mL of methanol was added.…”
Section: S3mentioning
confidence: 99%