Copper(i)-catalyzed intermolecular cyanoarylation of alkenes: convenient access to α-alkylated arylacetonitriles

被引:14
作者
Chen, Xin-Jie [1 ]
Gui, Qing-Wen [3 ]
Yi, Rongnan [2 ]
Yu, Xianyong [1 ]
Wu, Zhi-Lin [4 ]
Huang, Ying [3 ]
Cao, Zhong [3 ]
He, Wei-Min [3 ]
机构
[1] Hunan Univ Sci & Technol, Minist Educ, Sch Chem & Chem Engn, Key Lab Theoret Organ Chem & Funct Mol, Xiangtan 411201, Peoples R China
[2] Hunan Univ, Dept Chem, Changsha 410082, Hunan, Peoples R China
[3] Changsha Univ Sci & Technol, Hunan Prov Key Lab Mat Protect Elect Power & Rans, Changsha 410114, Peoples R China
[4] Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China
关键词
DIARYLIODONIUM SALTS; CASCADE ANNULATION; REGIOSELECTIVE SYNTHESIS; ARYLATION; NITRILES; PHOTOREDOX; QUINOXALIN-2(1H)-ONES; ALCOHOLS; CYANOALKYLATION; ALKYLNITRILES;
D O I
10.1039/d0ob01055c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel Cu(i)-catalyzed intermolecular cyanoarylation of alkenes with diaryliodonium salts as a radical arylating reagent andtetra-butylammonium cyanide as an electrophilic cyanating reagent was established. A broad range of alpha-alkylated arylacetonitriles were efficiently constructed in good to excellent yields under base- and oxidant-free and mild conditions.
引用
收藏
页码:5234 / 5237
页数:4
相关论文
共 64 条
[1]   Monoalkylation of Acetonitrile by Primary Alcohols Catalyzed by Iridium Complexes [J].
Anxionnat, Bruno ;
Pardo, Domingo Gomez ;
Ricci, Gino ;
Cossy, Janine .
ORGANIC LETTERS, 2011, 13 (15) :4084-4087
[2]   Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran [J].
Bao, Wen-Hu ;
Wang, Zheng ;
Tang, Xiao ;
Zhang, Yun-Fu ;
Tan, Jia-Xi ;
Zhu, Qin ;
Cao, Zhong ;
Lin, Ying-Wu ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2259-2262
[3]   Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis [J].
Borghs, Jannik C. ;
Mai Anh Tran ;
Sklyaruk, Jan ;
Rueping, Magnus ;
El-Sepelgy, Osama .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :7927-7935
[4]   Osmium Catalyst for the Borrowing Hydrogen Methodology: α-Alkylation of Arylacetonitriles and Methyl Ketones [J].
Buil, Maria L. ;
Esteruelas, Miguel A. ;
Herrero, Juana ;
Izquierdo, Susana ;
Pastor, Isidro M. ;
Yus, Miguel .
ACS CATALYSIS, 2013, 3 (09) :2072-2075
[5]   Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts [J].
Cahard, Elise ;
Male, Henry P. J. ;
Tissot, Matthieu ;
Gaunt, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) :7986-7989
[6]   The concept of dual roles design in clean organic preparation [J].
Cao, Zhong ;
Zhu, Qin ;
Lin, Ying-Wu ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2132-2138
[7]   A counteranion triggered arylation strategy using diaryliodonium fluorides [J].
Chan, L. ;
McNally, A. ;
Toh, Q. Y. ;
Mendoza, A. ;
Gaunt, M. J. .
CHEMICAL SCIENCE, 2015, 6 (02) :1277-1281
[8]   Oxidant-directed chemoselective sulfonylation and sulfonyloximation of alkenes via cleaving the C-S bond in TosMIC [J].
Chu, Xue-Qiang ;
Ge, Danhua ;
Loh, Teck-Peng ;
Shen, Zhi-Liang .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (06) :835-840
[9]   Monoalkylations with alcohols by a cascade reaction on bifunctional solid catalysts: Reaction kinetics and mechanism [J].
Corma, Avelino ;
Rodenas, Tania ;
Sabater, Maria J. .
JOURNAL OF CATALYSIS, 2011, 279 (02) :319-327
[10]   Copper-Catalyzed Arylation with Diaryliodonium Salts [J].
Fananas-Mastral, Martin .
SYNTHESIS-STUTTGART, 2017, 49 (09) :1905-1930