DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates

被引:7
作者
Cheng, Ming-Xing [1 ]
Lei, Jing-Wei [1 ]
Xie, Cai-Xia [1 ]
机构
[1] Henan Univ Chinese Med, Coll Pharm, 156 Jinshui East Rd, Zhengzhou 450046, Henan, Peoples R China
关键词
DDQ; cross-dehydrogenative-coupling; phosphonylation; allylic amines; dialkyl phosphonates; aminophosphonates; OXIDATIVE C-C; ALPHA-AMINOPHOSPHONATES; BIOLOGICAL-PROPERTIES; ACID; PHOSPHONYLATION; PHOSPHONOPEPTIDES; INHIBITORS; STRATEGY; BINDING; ESTERS;
D O I
10.1055/s-0037-1611362
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work reports a DDQ-mediated cross-dehydrogenative-coupling reaction of secondary amines with dialkyl phosphonates under mild conditions. This reaction proceeds efficiently without involving visible light or transition-metal catalysis. This new approach provides efficient access to biologically important -aminophosphonates.
引用
收藏
页码:114 / 118
页数:5
相关论文
共 40 条
[1]   CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164
[2]   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
[3]   PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].
ALLEN, JG ;
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
HOLMES, SW ;
LAMBERT, RW ;
NISBET, LJ ;
RINGROSE, PS .
NATURE, 1978, 272 (5648) :56-58
[4]  
Alonso E, 2000, SYNLETT, P698
[5]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].
ATHERTON, FR ;
HASSALL, CH ;
LAMBERT, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40
[6]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126
[7]   Phosphatase inhibitors .3. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase [J].
Beers, SA ;
Schwender, CF ;
Loughney, DA ;
Malloy, E ;
Demarest, K ;
Jordan, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (10) :1693-1701
[8]   Iron-catalyzed aerobic oxidative phosphonation of N-aryl tetrahydroisoquinolines [J].
Cai, Junjie ;
Liu, Yingle ;
Jiang, Yan ;
Yang, Yi .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (09) :1068-1073
[9]   Chiral Bronsted Acid Catalyzed Enantioselective Phosphonylation of Allylamine via Oxidative Dehydrogenation Coupling [J].
Cheng, Ming-Xing ;
Ma, Ran-Song ;
Yang, Qiang ;
Yang, Shang-Dong .
ORGANIC LETTERS, 2016, 18 (13) :3262-3265
[10]   Catalyst-Free Cross-Dehydrogenative Coupling Strategy Using Air as an Oxidant: Synthesis of α-Aminophosphonates [J].
Dhineshkumar, Jayaraman ;
Samaddar, Prasanjit ;
Prabhu, Kandikere Ramaiah .
ACS OMEGA, 2017, 2 (08) :4885-4893