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

共 50 条

[21] Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions
Lu, Zhiyao
Cui, Yuxin
Jia, Yanxing
SYNTHESIS-STUTTGART, 2011, (16): : 2595 - 2599
[22] Palladium-Catalyzed Intramolecular Oxidative C-H Sulfuration of Aryl Thiocarbamates
Zhao, Yingwei
Xie, Yinjun
Xia, Chungu
Huang, Hanmin
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2471 - 2476
[23] Palladium-Catalyzed C-H Arylation of 1,2,3-Triazoles
Zhang, Chengwei
You, Lin
Chen, Chuo
MOLECULES, 2016, 21 (10)
[24] Remote C-H Functionalization by a Palladium-Catalyzed Transannular Approach
De Sarkar, Suman
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (36) : 10558 - 10560
[25] Palladium-Catalyzed Construction of Heteroatom-Containing π-Conjugated Systems by Intramolecular Oxidative C-H/C-H Coupling Reaction
Saito, Kenta
Chikkade, Prasanna Kumara
Kanai, Motomu
Kuninobu, Yoichiro
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (23) : 8365 - 8368
[26] Mechanistic Investigation of Palladium-Catalyzed Allylic C-H Activation
Engelin, Casper
Jensen, Thomas
Rodriguez-Rodriguez, Sergio
Fristrup, Peter
ACS CATALYSIS, 2013, 3 (03): : 294 - 302
[27] Palladium-Catalyzed Direct C-H Arylation of Cyclic Enaminones with Aryl Iodides
Yu, Yi-Yun
Bi, Lei
Georg, Gunda I.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12) : 6163 - 6169
[28] Palladium-Catalyzed Decarboxylative Arylation of C-H Bonds by Aryl Acylperoxides
Yu, Wing-Yiu
Sit, Wing Nga
Zhou, Zhongyuan
Chan, Albert S. -C.
ORGANIC LETTERS, 2009, 11 (15) : 3174 - 3177
[29] Palladium-catalyzed carbonylative C-H activation of arenes with norbornene as the coupling partner
Chen, Jianbin
Natte, Kishore
Wu, Xiao-Feng
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 803 : 9 - 12
[30] Palladium-Catalyzed C8-Arylation of Naphthalenes through C-H Activation: A Combined Experimental and Computational Study
Garrec, Julian
Cordier, Marie
Frison, Gilles
Prevost, Sebastien
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (63) : 14441 - 14446

← 1 2 3 4 5 →