Palladium- and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides

被引：83

作者：

Yao, Tomoyuki ^{[1
]}

Hirano, Koji ^{[1
]}

Satoh, Tetsuya ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 41期

关键词：

alkylation; azoles; C-H activation; nickel; palladium; C-H BOND; CROSS-COUPLING REACTIONS; GACL3-CATALYZED ORTHO-ETHYNYLATION; DIRECT ARYLATION; DIRECT ALKYNYLATION; CARBON-HYDROGEN; HIGHLY EFFICIENT; SUZUKI REACTIONS; ALKENYLATION; COPPER;

D O I：

10.1002/chem.201001631

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Long-ing alkyl chain: The catalytic direct C-H alkylation of azoles with unactivated alkyl bromides and chlorides is described. A palladium catalyst enables the alkylation of oxazoles, whereas a nickel one shows unique activity for thiazole. The catalyses allow a straightforward access to azole motifs bearing long, functional alkyl side chains. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12307 / 12311

页数：5

共 50 条

[1] Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)2
Xia, Aiyou
Xie, Xin
Chen, Haoyi
Zhao, Jidong
Zhang, Chunli
Liu, Yuanhong
ORGANIC LETTERS, 2018, 20 (23) : 7735 - 7739
[2] Nickel-Catalyzed Reductive Amidation of Unactivated Alkyl Bromides
Serrano, Eloisa
Martin, Ruben
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) : 11207 - 11211
[3] Alkylboronic Esters from Palladium- and Nickel-Catalyzed Borylation of Primary and Secondary Alkyl Bromides
Yi, Jun
Liu, Jin-Hui
Liang, Jun
Dai, Jian-Jun
Yang, Chu-Ting
Fu, Yao
Liu, Lei
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) : 1685 - 1691
[4] Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides
Matsuyama, Naoto
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
ORGANIC LETTERS, 2009, 11 (18) : 4156 - 4159
[5] Nickel-Catalyzed Direct Arylation of Azoles with Aryl Bromides
Hachiya, Hitoshi
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
ORGANIC LETTERS, 2009, 11 (08) : 1737 - 1740
[6] Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides
Fang, Yi
Rogge, Torben
Ackermann, Lutz
Wang, Shun-Yi
Ji, Shun-Jun
NATURE COMMUNICATIONS, 2018, 9
[7] Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides
Yi Fang
Torben Rogge
Lutz Ackermann
Shun-Yi Wang
Shun-Jun Ji
Nature Communications, 9
[8] Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides
Wang, Fei
Rao, Weidong
Wang, Shun-Yi
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13): : 8970 - 8979
[9] Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes
Cruz, Cole L.
Montgomery, John
CHEMICAL SCIENCE, 2021, 12 (36) : 11995 - 12000
[10] Nickel-Catalyzed Reductive Coupling of γ-Metalated Ketones with Unactivated Alkyl Bromides
Cui, Ning
Lin, Tingzhi
Wang, Yan-En
Wu, Jian
Han, Yuheng
Xu, Xinyang
Xue, Fei
Xiong, Dan
Walsh, Patrick J.
Mao, Jianyou
ORGANIC LETTERS, 2022, 24 (22) : 3987 - 3992

← 1 2 3 4 5 →