Synthesis of masked haloareneboronic acids via iridium-catalyzed aromatic C-H borylation with 1,8-naphthalenediaminatoborane (danBH)

被引:84
作者
Iwadate, Noriyuki [1 ]
Suginome, Michinori [1 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Grad Sch Engn, Nishikyo Ku, Kyoto 6068501, Japan
关键词
C-H borylation; Iridium catalysis; Cross-coupling; Iterative synthesis; Dendrimer synthesis; CROSS-COUPLING REACTION; ROOM-TEMPERATURE; HYDROXYPHENYLBORONIC ACIDS; ORGANOBORON COMPOUNDS; COMPLEXES; FUNCTIONALIZATION; OLIGOARENES; ARENES; ESTERS; PINACOLBORANE;
D O I
10.1016/j.jorganchem.2008.11.068
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
"Masked" areneboronic acids have been prepared by Ir-catalyzed C-H borylation of arenes. A [Ir(OMe)(cod)](2) complex with a DPPE ligand showed the highest catalytic activity in the C-H borylation of benzene at 80 degrees C. The reaction system can be applied to substituted arenes, including halogen-substituted arenes. 1,3-Dihalobenzenes undergo the C-H borylation at their 5-positions in a regioselective fashion, affording 3,5-dihaloareneboronic acid derivatives, which serve as useful coupling modules for the convergent dendrimer synthesis. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:1713 / 1717
页数:5
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