Synthesis of corannulene and alkyl derivatives of corannulene

被引:230
作者
Seiders, TJ [1 ]
Elliott, EL [1 ]
Grube, GH [1 ]
Siegel, JS [1 ]
机构
[1] Univ Calif San Diego, Dept Chem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ja991310o
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of corannulene and alkyl corannulene derivatives has been accomplished using solution-phase chemistry. The key step in the synthesis is the coupling of benzylic bromides of 1,6,7,10-tetraalkylfluoranthene derivatives by low-valent titanium to construct the corannulene nucleus. The use of low-valent titanium represents a viable alternative to flash vacuum pyrolysis methods previously developed. Corannulene (1), methylcorannulene (8), three different dimethylcorannulenes (2, 3, 5), two different tetramethylcorannulenes (4, 6), acecorannulylene (7), C-5h symmetric pentamethylcorannulene (9), and decamethylcorannulene (10) have been prepared using low-valent titanium carbon-carbon coupling chemistry and halogen for alkyl exchange chemistry mediated by trimethylaluminum and catalytic nickel salts.
引用
收藏
页码:7804 / 7813
页数:10
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