Nickel-Catalyzed Reductive Three-Component Cross-Coupling of Butadiene with Aldehydes and Alkenyl Triflates/Bromides: Access to Skipped Dienes

被引：0

作者：

Xu, Yan ^{[1
]}

Su, Tong ^{[1
]}

Zhang, Jie-Rui ^{[1
]}

Ding, Hua-Jiao ^{[1
]}

Gao, Yuanji ^{[1
]}

Xu, Minghui ^{[1
]}

Cao, Peng ^{[1
]}

Hu, Ping ^{[1
]}

Wang, Bi-Qin ^{[1
]}

Chen, Bin ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 17期

关键词：

1,3-DIENES; HALIDES; ACIDS;

D O I：

10.1021/acs.orglett.3c01036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio-and stereoselective nickel-catalyzed reductive three-component cross-coupling of 1,3-butadiene with aldehydes and alkenyl triflates or bromides was realized. This protocol afforded a convenient approach to the synthesis of skipped diene compounds bearing various functionals and heterocyclic groups. The utility of this reaction was also demonstrated by scale-up preparation and diverse transformations.

引用

页码：3136 / 3140

页数：5

共 50 条

[31] Nickel-Catalyzed Cross-Coupling of Ethyl Chlorofluoroacetate with Aryl Bromides
Li, Han
Sheng, Jie
Wu, Bing-Bing
Li, Yan
Wang, Xi-Sheng
CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (13) : 1741 - 1744
[32] Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides
Zhu, Mingxiang
Alami, Mouad
Messaoudi, Samir
CHEMICAL COMMUNICATIONS, 2020, 56 (32) : 4464 - 4467
[33] Nickel-Catalyzed Ring-Opening Three-Component Coupling of Methylenecyclopropane with Aldehydes and Silanes
Ogata, Kenichi
Atsuumi, Yuka
Fukuzawa, Shin-ichi
ORGANIC LETTERS, 2010, 12 (20) : 4536 - 4539
[34] Reactivity in Nickel-Catalyzed Multi-component Sequential Reductive Cross-Coupling Reactions
Chen, Haifeng
Yue, Huifeng
Zhu, Chen
Rueping, Magnus
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (33)
[35] Nickel-Catalyzed Three-Component Cycloadditions of Enoates, Alkynes, and Aldehydes
Jenkins, Aireal D.
Robo, Michael T.
Zimmerman, Paul M.
Montgomery, John
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 2956 - 2965
[36] Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes
Poremba, Kelsey E.
Kadunce, Nathaniel T.
Suzuki, Naoyuki
Cherney, Alan H.
Reisman, Sarah E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (16) : 5684 - 5687
[37] Nickel-Catalyzed Three-Component Alkylarylation of Alkenyl N-Heteroarenes
Long, Teng
Zeng, Ya-Li
Dong, Zhi-Hong
Li, Shu
Zhan, Jie
Zeng, Sheng-Min
Qiu, Jia-Li
Chu, Wen-Dao
Liu, Quan-Zhong
ORGANIC LETTERS, 2023, 25 (46) : 8344 - 8349
[38] Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides
Yu, Xiaolong
Yang, Tao
Wang, Shulin
Xu, Hailiang
Gong, Hegui
ORGANIC LETTERS, 2011, 13 (08) : 2138 - 2141
[39] Nickel-Catalyzed Reductive Cross-Coupling of Aziridines and Allylic Chlorides
Liu, Shuai
Wang, Sen-Lin
Wan, Jie
Peng, Shuang
Zhang, Jie-Rui
Ding, Hua-Jiao
Zhang, Bin
Ni, Hai-Liang
Cao, Peng
Hu, Ping
Wang, Bi-Qin
Chen, Bin
ORGANIC LETTERS, 2023, 25 (35) : 6582 - 6586
[40] Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
Woods, Brian P.
Orlandi, Manuel
Huang, Chung-Yang
Sigman, Matthew S.
Doylet, Abigail G.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (16) : 5688 - 5691

← 1 2 3 4 5 →