Synthesis of Aryl Nitriles via Aerobic Oxidative Cleavage of Aryl C=C Bonds with (NH 4 ) 2 CO 3 as the Nitrogen Source

被引:5
作者
Zheng, Yi [1 ]
Liu, Wenbo [1 ]
Tian, Xinzhe [1 ]
Ren, Yun-Lai [1 ]
机构
[1] Henan Agr Univ, Coll Sci, Zhengzhou 450002, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
aromatic nitriles; arylethenes; carbon-carbon double bonds; oxidative cleavage; oxygen; ACCEPTORLESS DEHYDROGENATION; HETEROGENEOUS CATALYST; AROMATIC NITRILES; H BONDS; CYANATION; CONVERSION; ACCESS; AMINES; ACIDS; BENZONITRILES;
D O I
10.1055/s-0041-1737761
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An aerobic oxidative method was developed for conversion of arylethenes to aromatic nitriles using (NH4)2CO3as the nitrogen source and Cu(NO3)2as the catalyst. The present method allowed a series of arylethenes to underwent oxidative cleavage of C=C bonds to give the targeted products in low to high yields. In addition, the present conditions are compatible with many groups such as alkyl, alkoxy, N,Ndimethylamino, chloro, bromo, iodo, ester, cyano group, and so on. © 2022 Georg Thieme Verlag. All rights reserved.
引用
收藏
页码:376 / 380
页数:5
相关论文
共 69 条
[41]   A mineralogically-inspired silver-bismuth hybrid material: an efficient heterogeneous catalyst for the direct synthesis of nitriles from terminal alkynes [J].
Otvos, Sandor B. ;
Meszaros, Rebeka ;
Varga, Gabor ;
Kocsis, Marianna ;
Konya, Zoltan ;
Kukovecz, Akos ;
Pusztai, Peter ;
Sipos, Pal ;
Palinko, Istvan ;
Fulop, Ferenc .
GREEN CHEMISTRY, 2018, 20 (05) :1007-1019
[42]   Heterogeneous Catalytic Aqueous Phase Oxidative Cleavage of Styrenes to Benzaldehydes: An Environmentally Benign Alternative to Ozonolysis [J].
Schafer, Christian ;
Ellstrom, Clifford J. ;
Torok, Bela .
TOPICS IN CATALYSIS, 2018, 61 (7-8) :643-651
[43]   A novel oxidative procedure for the synthesis of benzamides from styrenes and amines under metal-free conditions [J].
Sharif, Muhammad ;
Gong, Jin-Long ;
Langer, Peter ;
Beller, Matthias ;
Wu, Xiao-Feng .
CHEMICAL COMMUNICATIONS, 2014, 50 (36) :4747-4750
[44]   Organophotoredox assisted cyanation of bromoarenes via silyl-radical-mediated bromine abstraction [J].
Shee, Maniklal ;
Shah, Sk. Sheriff ;
Singh, N. D. Pradeep .
CHEMICAL COMMUNICATIONS, 2020, 56 (30) :4240-4243
[45]   Nitric-Acid-Catalyzed Aerobic Conversion of Benzyl Ethers to Benzaldehydes at Room Temperature [J].
Shen, Zhenpeng ;
Zhao, Zhe ;
Ren, Yun-Lai ;
Liu, Wenbo ;
Tian, Xinzhe ;
Zheng, Xin ;
Zhao, Bo .
CHEMISTRYSELECT, 2020, 5 (45) :14288-14291
[46]   Iron-Promoted Decarboxylation of Arylacetic Acids for the Synthesis of Aromatic Nitriles with Sodium Nitrite as the Nitrogen Source [J].
Shen, Zhenpeng ;
Liu, Wenbo ;
Tian, Xinzhe ;
Zhao, Zhe ;
Ren, Yun-Lai .
SYNLETT, 2020, 31 (18) :1805-1808
[47]   Aerobic Oxidative C(CO)-C Bond Cleavage under Catalyst-Free and Additive-Free Conditions [J].
Tian, Xinzhe ;
Ren, Yun-Lai ;
Cheng, Xinqiang ;
Lu, Weiwei .
CHEMISTRYSELECT, 2019, 4 (39) :11496-11499
[48]   Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine [J].
Ueda, Yohei ;
Tsujimoto, Nagataka ;
Yurino, Taiga ;
Tsurugi, Hayato ;
Mashima, Kazushi .
CHEMICAL SCIENCE, 2019, 10 (04) :994-999
[49]   An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions [J].
Uludag, N. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (09) :1640-1645
[50]   TEMPO-catalyzed Aerobic Oxygenation and Nitrogenation of Olefins via C=C Double-Bond Cleavage [J].
Wang, Teng ;
Jiao, Ning .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) :11692-11695