Nickel-catalyzed reductive 1,1-diarylation of unactivated alkenes with aryl iodides

被引:4
作者
Wang, Zhengwen [1 ]
Jin, Zhou [1 ]
Zhou, Bingwei [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
基金
中国国家自然科学基金;
关键词
REMOTE FUNCTIONALIZATION; HALIDES;
D O I
10.1039/d3qo01812a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here we present a nickel-catalyzed reductive 1,1-diarylation reaction of unactivated alkenes with aryl iodides. 2,9-Dibutyl-1,10-phenanthroline was determined to be an optimal ligand for controlling the chemo-/regioselectivity towards 1,1-diarylated products. Aliphatic terminal alkenes bearing, respectively, ester, aryloxy and amino groups at the distal position were found to be competent for the 1,1-diarylation reaction, providing the terminal diarylated esters, ethers and amines in moderate to good yields.
引用
收藏
页码:1382 / 1387
页数:6
相关论文
共 35 条
[21]   Nickel-Catalyzed Dicarbofunctionalization of Alkenes [J].
Qi, Xiaoxu ;
Diao, Tianning .
ACS CATALYSIS, 2020, 10 (15) :8542-8556
[22]   Reductive-Delay Heck 1,1-Diarylation of Terminal Alkenes [J].
Shao, Huihui ;
Zhao, Yao ;
Wang, Shuangqiang ;
Chen, Rizhi ;
Zhou, Jianrong Steve ;
Wu, Xiaojin .
ORGANIC LETTERS, 2022, :6520-6524
[23]   Ni-Catalyzed Reductive Dicarbofunctionalization of Nonactivated Alkenes: Scope and Mechanistic Insights [J].
Shu, Wei ;
Garcia-Dominguez, Andres ;
Quiros, M. Teresa ;
Mondal, Rahul ;
Cardenas, Diego J. ;
Nevado, Cristina .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (35) :13812-13821
[24]   Walking Metals for Remote Functionalization [J].
Sommer, Heiko ;
Julia-Hernandez, Francisco ;
Martin, Ruben ;
Marek, Ilan .
ACS CENTRAL SCIENCE, 2018, 4 (02) :153-165
[25]   Integrating aryl chlorides into nickel-catalyzed 1,1-difunctionalization of alkenes [J].
Sun, Caocao ;
Yin, Guoyin .
CHINESE CHEMICAL LETTERS, 2022, 33 (12) :5096-5100
[26]   Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes [J].
Talavera, Laura ;
Freund, Robert R. A. ;
Zhang, Huihui ;
Wakeling, Matthew ;
Jensen, Mara ;
Martin, Ruben .
ACS CATALYSIS, 2023, 13 (08) :5538-5543
[27]   Mechanistic Analysis of Metallaphotoredox C-N Coupling: Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity [J].
Till, Nicholas A. ;
Tian, Lei ;
Dong, Zhe ;
Scholes, Gregory D. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (37) :15830-15841
[28]  
Vasseur A, 2016, NAT CHEM, V8, P209, DOI [10.1038/NCHEM.2445, 10.1038/nchem.2445]
[29]   Nickel-Catalyzed Reductive Couplings [J].
Wang, Xuan ;
Dai, Yijing ;
Gong, Hegui .
TOPICS IN CURRENT CHEMISTRY, 2016, 374 (04)
[30]   Methods and Mechanisms for Cross-Electrophile Coupling of Csp2 Halides with Alkyl Electrophiles [J].
Weix, Daniel J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (06) :1767-1775