Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

被引:10
作者
He, Tianyu [1 ]
Chen, Dengfeng [1 ]
Qian, Shencheng [1 ]
Zheng, Yu [1 ]
Huang, Shenlin [1 ]
机构
[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Coll Chem Engn, Nanjing 210037, Jiangsu, Peoples R China
基金
中国博士后科学基金;
关键词
SODIUM-NITRITE; KETONES; ACTIVATION; OXIDATION;
D O I
10.1021/acs.orglett.1c02327
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.
引用
收藏
页码:6525 / 6529
页数:5
相关论文
共 47 条
[1]   EUDESMANOLIDES AND OTHER CONSTITUENTS FROM ARTEMISIA-HERBA-ALBA [J].
AHMED, AA ;
ABOUELELA, M ;
JAKUPOVIC, J ;
ELDIN, AAS ;
SABRI, N .
PHYTOCHEMISTRY, 1990, 29 (11) :3661-3663
[2]   Oxidative aliphatic carbon-carbon bond cleavage reactions [J].
Allpress, Caleb J. ;
Berreau, Lisa M. .
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) :3005-3029
[3]   Metal Nitrite: A Powerful Oxidizing Reagent [J].
Baidya, Mahiuddin ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) :13880-13882
[4]   Catalytic oxidative carbon-carbon bond cleavage of ketones with dioxygen:: assessment of some metal complexes.: Some alternatives for preparing α, ω-dicarboxylic acids [J].
Brégeault, JM ;
Launay, F ;
Atlamsani, A .
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (01) :11-26
[5]   Synthesis of Spiroisoxazolines via TEMPO/NaNO2-Catalyzed Aerobic Oxidative Dearomatization [J].
Chen, Dengfeng ;
Wang, Yaming ;
Cai, Xu-Min ;
Cao, Xiaoji ;
Jiang, Ping ;
Wang, Fei ;
Huang, Shenlin .
ORGANIC LETTERS, 2020, 22 (17) :6847-6851
[6]   Synthesis of Spiroisoxazolines via an Oximation/Dearomatization Cascade under Air [J].
Chen, Dengfeng ;
He, Tianyu ;
Huang, Yuan ;
Luo, Jinyue ;
Wang, Fei ;
Huang, Shenlin .
ORGANIC LETTERS, 2020, 22 (11) :4429-4434
[7]   Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].
Chen, Feng ;
Wang, Teng ;
Jiao, Ning .
CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661
[8]   "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation [J].
Chen, Peng-hao ;
Billett, Brent A. ;
Tsukamoto, Tatsuhiro ;
Dong, Guangbin .
ACS CATALYSIS, 2017, 7 (02) :1340-1360
[9]   Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis [J].
Chen, Yilin ;
Du, Jianbo ;
Zuo, Zhiwei .
CHEM, 2020, 6 (01) :266-279
[10]   Cleavage of C(aryl)-CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions [J].
Dai, Peng-Fei ;
Ning, Xiao-Shan ;
Wang, Hua ;
Cui, Xian-Chao ;
Liu, Jie ;
Qu, Jian-Ping ;
Kang, Yan-Biao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) :5392-5395