期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 14, 期 21, 页码 3850-3854出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201901155
关键词
alkoxysilanes; aryl bromides; aryltrialkoxysilanes; Hiyama coupling reaction; pincer complex; spirosilicates
资金
- JST-ACCEL program [JPMJAC1401]
- JSPS KAKENHI [17J05446]
- JSPS [17K14524]
- Mitsubishi Gas Chemical Company, Inc. (Mitsubishi Gas Chemical Award in Synthetic Organic Chemistry, Japan)
- Grants-in-Aid for Scientific Research [17J05446, 17K14524] Funding Source: KAKEN
A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS and NMR analyses of the reaction mixture suggested the formation of pentacoordinate spirosilicate intermediates in situ. Preliminary theoretical studies revealed that the glycol-derived silicate intermediates formed in situ are quite reactive silicon reagents in the transmetalation step.
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