期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 11, 期 11, 页码 1738-1746出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201600424
关键词
electrophilic substitution; fused-ring systems; porphyrinoids; sila-Friedel-Crafts reaction; silicon
资金
- MEXT [25107002]
- JSPS [25220802, 24685007, 26620081]
- ACT-C, JST
- Kansai Research Foundation for Technology Promotion
- Asahi Glass Foundation
- Global Research Laboratory (GRL) Program of the Ministry of Education, Science and Technology (MEST) of Korea [2013K1A1A2A02050183]
- Grants-in-Aid for Scientific Research [16K13952, 25107002] Funding Source: KAKEN
A reaction sequence of 2-(diphenylsilyl)phenylation by Negishi coupling and intramolecular sila-Friedel-Crafts reaction has been explored for the synthesis of monotriphenylsilane-fused porphyrins 5M and 6M (M= Ni, Zn) and bis-triphenylsilane-fused porphyrins 7M and 8Ni. A triply linked triphenylsilane-fused NiII porphyrin, 13Ni, was synthesized in a stepwise manner involving the above reaction sequence and a final Pd-catalyzed C-H activating arylative cyclization. The silicon atom in 13 Ni takes a distorted planarized structure with an almost perpendicular Si-phenyl group, causing an electronic effect due to effective sigma*-pi* interaction.
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