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

[21] DFT study on mechanism of nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides
Liu, Lijuan
Shang, Zhenfeng
Li, Ruifang
Xu, Xiufang
TETRAHEDRON LETTERS, 2024, 152
[22] Recent Developments in Transition-Metal Catalyzed Direct C-H Alkenylation, Alkylation, and Alkynylation of Azoles
Chen, Su
Ranjan, Prabhat
Voskressensky, Leonid G.
Van der Eycken, Erik V.
Sharma, Upendra K.
MOLECULES, 2020, 25 (21):
[23] Scope and Mechanistic Aspect of Nickel-Catalyzed Alkenylation of Benzothiazoles and Related Azoles with Styryl Bromides
Patel, Ulhas N.
Jagtap, Rahul A.
Punji, Benudhar
ORGANOMETALLICS, 2019, 38 (12) : 2422 - 2430
[24] Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis
He, Rong-De
Bai, Yunfei
Han, Guan-Yu
Zhao, Zhen-Zhen
Pang, Xiaobo
Pan, Xiaobo
Liu, Xue-Yuan
Shu, Xing-Zhong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (04)
[25] Nickel-Catalyzed Sonogashira Couplings: Extending the Reaction Scope to Aryl Bromides and Chlorides
Braconi, Elena
Godineau, Edouard
Smejkal, Tomas
Jackh, Simon
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (07) : 1551 - 1558
[26] A Versatile Ligand Platform for Palladium- and Nickel-Catalyzed Ethylene Copolymerization with Polar Monomers
Chen, Min
Chen, Changle
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (12) : 3094 - 3098
[27] Palladium- and nickel-catalyzed coupling reactions of α-bromoalkenylphosphonates with arylboronic acids and lithium alkenylborates
Kobayashi, Y
William, AD
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1749 - 1757
[28] Nickel-Catalyzed Remote Arylation of Alkenyl Aldehydes Initiated by Radical Alkylation with Tertiary α-Carbonyl Alkyl Bromides
Jin, Weiwei
Zhou, Yulu
Zhao, Ying
Ma, Qianqian
Kong, Lichun
Zhu, Gangguo
ORGANIC LETTERS, 2018, 20 (05) : 1435 - 1438
[29] Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides
Wang, Tian-Zhang
Guan, Yu-Qiu
Zhang, Tian-Yu
Liang, Yu-Feng
ADVANCED SCIENCE, 2024, 11 (09)
[30] Nickel-Catalyzed Site-Selective Alkylation of Unactivated C(sp3)-H Bonds
Wu, Xuesong
Zhao, Yan
Ge, Haibo
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (05) : 1789 - 1792

← 1 2 3 4 5 →