Iridium-Catalyzed ortho-Selective C-H Silylation of Aromatic Compounds Directed toward the Synthesis of π-Conjugated Molecules with Lewis Acid-Base Interaction

被引：32

作者：

Wakaki, Takayuki ^{[1
]}

Kanai, Motomu ^{[1
,2
]}

Kuninobu, Yoichiro ^{[1
,2
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

[2] Japan Sci & Technol Agcy JST, ERATO, Kanai Life Sci Catalysis Project, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 07期

关键词：

PLANAR CHIRAL FERROCENES; COORDINATION-NUMBER; ENANTIOSELECTIVE SYNTHESIS; INTRAMOLECULAR COMPLEXES; FLUORESCENT AZOBENZENES; ASYMMETRIC-SYNTHESIS; COMPOUNDS BEARING; AZO GROUP; BOND; SILICON;

D O I：

10.1021/acs.orglett.5b00529

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We successfully developed an iridium-catalyzed ortho-selective C-H silylation of aromatic compounds. The reaction exhibited a wide substrate scope, and a variety of pi-conjugated molecules were synthesized in good to excellent yields, even in gram scale. Several silyl groups could also be introduced into the products. The experimental results indicated that the regioselectivity could be controlled by a Lewis acid-base interaction between the Lewis acidic silicon atoms of fluorinated hydrosilanes and the Lewis basic nitrogen atoms of aromatic compounds.

引用

页码：1758 / 1761

页数：4

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