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
收藏
页码：2566 / 2572
页数：7
相关论文
共 50 条
  • [31] Palladium-Catalyzed C-H Arylation of [1,1'-Biphenyl]-2-ols with Chloroarenes
    Kinoshita, Keisuke
    Yamaguchi, Miyuki
    Sasou, Hirohisa
    Konishi, Hideyuki
    Manabe, Kei
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2023, 71 (02) : 175 - 182
  • [32] Palladium-catalyzed direct C-H arylation of ferrocenecarboxamides with aryl halides
    Qiao, Huijie
    Sun, Suyan
    Yang, Fan
    Zhu, Yu
    Zhu, Weiguo
    Wu, Yusheng
    Wu, Yangjie
    RSC ADVANCES, 2016, 6 (64) : 59319 - 59326
  • [33] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [34] Palladium-Catalyzed Direct Arylation of Cyclic Enamides with Aryl Silanes by sp2 C-H Activation
    Zhou, Hai
    Xu, Yun-He
    Chung, Wan-Jun
    Loh, Teck-Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (29) : 5355 - 5357
  • [35] Synthesis of Benzobis- and Benzotrisbenzofurans by Palladium-Catalyzed Multiple Intramolecular C-H/C-H Coupling
    Kaida, Hiroyuki
    Satoh, Tetsuya
    Nishii, Yuji
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY LETTERS, 2016, 45 (09) : 1069 - 1071
  • [36] Palladium-Catalyzed Direct C-H Arylation of Arenes Promoted by Quaternary Ammonium Salt
    Yang, Sabyuk
    Hong, Soon Hyeok
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (11) : 1846 - 1851
  • [37] Expeditious approach to the Amarylidaceae alkaloids, crinasiadine and its analogues, via a palladium-catalyzed intramolecular direct C-H arylation
    Mishra, Sourabh
    De, Subhadip
    Kakde, Badrinath N.
    Dey, Dhananjay
    Bisai, Alakesh
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 2013, 52 (8-9): : 1093 - 1102
  • [38] Palladium-Catalyzed Direct Arylation of Azulene Based on Regioselective C-H Bond Activation
    Murai, Masahito
    Yanagawa, Mayu
    Nakamura, Masahiro
    Takai, Kazuhiko
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) : 629 - 635
  • [39] Intramolecular Oxidative Palladium-Catalyzed Amination Involving Double C-H Functionalization of Unactivated Olefins
    Broggini, Gianluigi
    Borelli, Tea
    Giofre, Sabrina
    Mazza, Alberto
    SYNTHESIS-STUTTGART, 2017, 49 (13): : 2803 - 2818
  • [40] Palladium-Catalyzed C-F Bond Formation via Directed C-H Activation
    Li, Yan
    Wu, Yun
    Li, Guang-Shui
    Wang, Xi-Sheng
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1412 - 1418
12345