Iron-catalyzed aerobic oxidative phosphonation of N-aryl tetrahydroisoquinolines

被引:7
作者
Cai, Junjie [1 ]
Liu, Yingle [1 ]
Jiang, Yan [1 ]
Yang, Yi [1 ]
机构
[1] Sichuan Univ Sci & Engn, Coll Chem & Environm Engn, Key Lab Green Catalysis Higher Educ Inst Sichuan, 180 Xueyuan St,Huixing Rd, Zigong 643000, Sichuan, Peoples R China
基金
中国国家自然科学基金;
关键词
Oxidative phosphonation; iron catalysis; coupling; alpha-aminophosphonate; DEHYDROGENATIVE-COUPLING REACTIONS; C-H FUNCTIONALIZATION; BOND-FORMING REACTIONS; TERTIARY-AMINES; ALPHA-AMINOPHOSPHONATES; BIOLOGICAL-PROPERTIES; ANTITUMOR-ACTIVITY; ACID-DERIVATIVES; EFFICIENT; INHIBITORS;
D O I
10.1080/10426507.2017.1330827
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We report herein a novel and efficient method for iron-catalyzed aerobic oxidative phosphonation of N-aryl tetrahydroisoquinolines for the synthesis of biologically interesting alpha-aminophosphonates. This new C-P bond formation reaction features the employment of a sustainable and cost-effective iron salt [Fe(NO3)(3)center dot 9H(2)O] as catalyst, the utilization of air as environmental-benign oxidant, as well as the user-friendly open-flask reaction conditions.
引用
收藏
页码:1068 / 1073
页数:6
相关论文
共 72 条
[1]   Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C-H bonds: synthesis of α-aminophosphonates under aerobic conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
TETRAHEDRON LETTERS, 2012, 53 (12) :1456-1459
[2]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[3]  
Balali-Mood Mahdi., 2014, BASIC CLIN TOXICOLOG
[4]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126
[5]   Iron Catalysis in Organic Synthesis [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
CHEMICAL REVIEWS, 2015, 115 (09) :3170-3387
[6]   USE IN SYNTHESIS OF THE IMINIUM CATION GENERATED INSITU BY THE ELECTROCHEMICAL OXIDATION OF TERTIARY-AMINES [J].
BIDAN, G ;
GENIES, M .
TETRAHEDRON, 1981, 37 (12) :2297-2301
[7]   A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline [J].
Boess, Esther ;
Schmitz, Corinna ;
Klussmann, Martin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) :5317-5325
[8]   The direct α-C(sp3)-H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing [J].
Brzozowski, Martin ;
Forni, Jose A. ;
Savage, G. Paul ;
Polyzos, Anastasios .
CHEMICAL COMMUNICATIONS, 2015, 51 (02) :334-337
[9]   Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].
Campbell, Alison N. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863
[10]  
CHERKASOV RA, 1998, RUSS CHEM REV, V67, P857, DOI [DOI 10.1070/RC1998V067N10ABEH000421, 10.1070/RC1998v067n10ABEH000421]