Nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides

被引：13

作者：

Zhang, Yanling ^{[1
]}

Zhang, Zhiguo ^{[1
]}

Hu, Yuanyuan ^{[1
]}

Liu, Yunkui ^{[1
]}

Jin, Hongwei ^{[1
]}

Zhou, Bingwei ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 41期

基金：

中国国家自然科学基金;

关键词：

C-H CYANATION; ARYL HALIDES; EFFICIENT CATALYSTS; COUPLING REACTIONS; TERMINAL ALKYNES; NITRILES; MILD; PD; COMPLEXES; BROMIDES;

D O I：

10.1039/d2ob01240e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein describe a nickel-catalyzed cyanation reaction of aryl/alkenyl halides with alkyl isocyanides. Both aryl/alkenyl iodines and bromides were found to be competent electrophiles that reacted with alkyl isocyanides, affording nitrile compounds in moderate to good yields. A range of functional groups including halogens as well as hydroxyl, formyl, and acetamino groups were fairly compatible with the nickel catalysis. This protocol featured broad functional group tolerance, simple reaction conditions, and gram-scale synthesis.

引用

页码：8049 / 8053

页数：5

共 50 条

[31] Ketone Formation via Mild Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Aryl Acid Chlorides
Wu, Fan
Lu, Wenbin
Qian, Qun
Ren, Qinghua
Gong, Hegui
ORGANIC LETTERS, 2012, 14 (12) : 3044 - 3047
[32] 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
[33] Nickel-Catalyzed Amination of (Hetero)aryl Halides Facilitated by a Catalytic Pyridinium Additive
Han, Dongyang
Li, Sasa
Xia, Siqi
Su, Mincong
Jin, Jian
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (54) : 12349 - 12354
[34] Nickel-Catalyzed Heck Reaction of Aryl Halides and Terminal Olefins Using Zinc/Triflate Ligand/DMA/TBAB
Mishra, Satyendra
Halpani, Chandni G.
Patel, Sejal
CHEMISTRYSELECT, 2019, 4 (23): : 6913 - 6916
[35] Nickel-catalyzed Mizoroki-Heck cross-coupling reaction of aryl halides with styrenes
Bhange, Dattatraya Soma
Rasal, Nishant Kisan
INDIAN JOURNAL OF CHEMISTRY, 2024, 63 (08): : 823 - 829
[36] Nickel-catalyzed electrochemical reductive relay cross-coupling of alkyl halides with alkyl carboxylic acids
Jiao, Ke-Jin
Ma, Cong
Liu, Dong
Qiu, Hui
Cheng, Bin
Mei, Tian-Sheng
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23) : 6603 - 6608
[37] Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides
Zhu, Dianhu
Lv, Leiyang
Qu, Zihang
Li, Chao-Jun
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) : 6312 - 6322
[38] Nickel-catalyzed electrochemical coupling of aryl, heteroaryl or vinyl halides with activated alkyl chlorides:: Synthetic and stereochemical aspects
Durandetti, M
Périchon, J
SYNTHESIS-STUTTGART, 2004, (18): : 3079 - 3083
[39] Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations
Gu, Jun
Wang, Xuan
Xue, Weichao
Gong, Hegui
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1411 - 1421
[40] Nickel-catalyzed direct C-H arylation of unactivated arenes with aryl halides
Xie, Guanlei
Li, Tingyi
Qu, Xiaoming
Mao, Jincheng
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 340 (1-2) : 48 - 52

← 1 2 3 4 5 →