Probing the mechanism of the Heck reaction with arene diazonium salts by electrospray mass and tandem mass spectrometry

被引:247
作者
Sabino, AA [1 ]
Machado, AHL [1 ]
Correia, CRD [1 ]
Eberlin, MN [1 ]
机构
[1] UNICAMP, Inst Chem, BR-13083970 Campinas, SP, Brazil
关键词
Heck reaction; homogeneous catalysis; mass spectrometry; reaction mechanisms; reactive intermediates;
D O I
10.1002/anie.200353076
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Key ionic intermediates of the Heck reaction of arene diazonium salts have been intercepted and structurally characterized by ESI-MS/MS. The use of electrospray ionization enables the ionic species to be transferred smoothly to the gas phase. A catalytic cycle for this reaction involving all the Pd cationic species intercepted has been proposed (see scheme).
引用
收藏
页码:2514 / 2518
页数:5
相关论文
共 47 条
[11]  
Chen P., 2003, ANGEW CHEM, V115, P2938, DOI DOI 10.1002/ANGE.200200560
[12]  
COLE RB, 1997, ELECTROSCOPY IONIZAT
[13]   Chiroselective self-directed octamerization of serine: Implications for homochirogenesis [J].
Cooks, RG ;
Zhang, DX ;
Koch, KJ ;
Gozzo, FC ;
Eberlin, MN .
ANALYTICAL CHEMISTRY, 2001, 73 (15) :3646-3655
[14]   Intrinsic gas-phase electrophilic reactivity of cyclic N-alkyl- and N-acyliminium ions [J].
D'Oca, MGM ;
Moraes, LAB ;
Pilli, RA ;
Eberlin, MN .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :3854-3864
[15]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[16]  
de Meijere A, 1994, ANGEW CHEM, V106, P2473, DOI DOI 10.1002/ANGE.19941062307
[17]  
de Vries AHM, 2002, ADV SYNTH CATAL, V344, P996, DOI 10.1002/1615-4169(200210)344:9<996::AID-ADSC996>3.0.CO
[18]  
2-J
[19]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963
[20]  
EBERLIN MN, UNPUB ORG LETT