Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles

被引:69
作者
He, L
Chan, PWH
Tsui, WM
Yu, WY
Che, CM
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, Open Lab Chem Biol, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1021/ol049232j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH2Cl2, 4 Angstrom molecular sieves, ultrasound, 40 degreesC) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.
引用
收藏
页码:2405 / 2408
页数:4
相关论文
共 22 条
[1]   Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study [J].
Au, SM ;
Huang, JS ;
Yu, WY ;
Fung, WH ;
Che, CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9120-9132
[2]   Studies on isocyanides and related compounds. Synthesis of 1-aryl-2-(tosylamino)-1H-imidazoles, a novel class of imidazole derivatives [J].
Bossio, R ;
Marcaccini, S ;
Pepino, R .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2202-2203
[3]   INTRAMOLECULAR NITRENE C-H INSERTIONS MEDIATED BY TRANSITION-METAL COMPLEXES AS NITROGEN ANALOGS OF CYTOCHROME-P-450 REACTIONS [J].
BRESLOW, R ;
GELLMAN, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6728-6729
[4]  
Breslow R., 1982, CHEM COMMUN, P1400
[5]  
DFAZREQUEJO MM, 2003, J AM CHEM SOC, V125, P12078
[6]   Catalytic intramolecular addition of metal carbenes to remote furans [J].
Doyle, MP ;
Chapman, BJ ;
Hu, WH ;
Peterson, CS ;
McKervey, MA ;
Garcia, CF .
ORGANIC LETTERS, 1999, 1 (09) :1327-1329
[7]  
Espino CG, 2001, ANGEW CHEM INT EDIT, V40, P598, DOI 10.1002/1521-3773(20010202)40:3<598::AID-ANIE598>3.0.CO
[8]  
2-9
[9]   Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation [J].
Espino, CG ;
Wehn, PM ;
Chow, J ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6935-6936
[10]   Synthetic studies toward the guanacastepenes [J].
Hughes, CC ;
Kennedy-Smith, JJ ;
Trauner, D .
ORGANIC LETTERS, 2003, 5 (22) :4113-4115