Palladium-Catalyzed Intramolecular C-H Arylation versus 1,5-Palladium Migration: A Theoretical Investigation

被引：18

作者：

Misawa, Nana ^{[1
]}

Tsuda, Tomohiro ^{[2
]}

Shintani, Ryo ^{[2
]}

Yamashita, Koichi ^{[3
]}

Nozaki, Kyoko ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1138656, Japan

[2] Osaka Univ, Grad Sch Engn Sci, Div Chem, Dept Mat Engn Sci, Toyonaka, Osaka 5608531, Japan

[3] Univ Tokyo, Sch Engn, Dept Chem Syst Engn, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1138656, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2018年 / 13卷 / 17期

关键词：

arylation; chemoselectivity; density functional calculations; C-H activation; palladium; DENSITY-FUNCTIONAL THEORY; ASYMMETRIC-SYNTHESIS; 1,4-PALLADIUM MIGRATION; BOND ACTIVATION; EFFICIENT SYNTHESIS; AROMATIC RINGS; ARYL BROMIDES; RHODIUM; CYCLIZATION; COMPLEXES;

D O I：

10.1002/asia.201800603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Theoretical investigations were carried out to elucidate the origin of chemoselectivity in the palladium-catalyzed reactions of 2-(dimethylphenylsilyl)phenyl triflates with or without an amino group at the 3-position. The selective formation of a 5,10-dihydrophenazasiline rather than a dibenzosilole from the substrate with an amino group at the 3-position could be successfully explained by proposing a new 1,5-palladium migration pathway that involves a neutral diorganopalladium(II) intermediate along with the subsequent formation of a low-energy amine-coordinated palladacycle intermediate prior to the C-N bond-forming process.

引用

页码：2566 / 2572

页数：7

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