Iridium-Catalyzed Direct Tetraborylation of Perylene Bisimides

被引：99

作者：

Teraoka, Takuro ^{[1
]}

Hiroto, Satoru ^{[1
]}

Shinokubo, Hiroshi ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 10期

关键词：

C-H ACTIVATION; BOND FUNCTIONALIZATION; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; BORYLATION; ESTERS; CONVERSION; PHENOLS; ARENES; DYES;

D O I：

10.1021/ol2004534

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of perylene bisimides (PBIs) with bls(pinacolato)diboron in the presence of an iridium catalyst provides tetraborylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The planar structure of the perylene core has been confirmed by X-ray diffraction analysis. Oxidation of tetraborylated PBI with hydroxylamine hydrochloride affords tetrahydroxy PBI In excellent yield, which exhibits a substantially blue-shifted absorption spectrum due to an Intramolecular hydrogenbonding interaction between carbonyl and hydroxy groups.

引用

页码：2532 / 2535

页数：4

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