Hydrogen Peroxide Promoted Mizoroki-Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes

被引:17
作者
Lasch, Roman [1 ]
Fehler, Stefanie K. [1 ]
Heinrich, Markus R. [1 ]
机构
[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, Pharmaceut Chem, Schuhstr 19, D-91052 Erlangen, Germany
关键词
PALLADIUM-CATALYZED VINYLATION; DIAZONIUM SALTS; MEERWEIN ARYLATION; COUPLING REACTIONS; ARYLBORONIC ACIDS; ARYL; MECHANISM; OLEFINS; COMPLEX; RHODIUM;
D O I
10.1021/acs.orglett.6b00449
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mizoroki-Heck reactions, which are well-known for aryldiazonium salts and which have recently been described for arylhydrazines, have now been extended to phenyldiazenes. In situ generation of phenyldiazenes from azocarboxylates allowed clean and selective reactions with styrenes, acrylates, and acrylamides using palladium(II) acetate in the presence of silver(I) acetate or hydrogen peroxide as oxidant. Hydrogen peroxide was thereby shown to be a cheap and broadly applicable alternative for the established palladium-silver(I) system.
引用
收藏
页码:1586 / 1589
页数:4
相关论文
共 61 条
[1]   Palladium-Silver Cooperativity in an Aryl Amination Reaction through C-H Functionalization [J].
Anand, Megha ;
Sunoj, Raghavan B. ;
Schaefer, Henry F., III .
ACS CATALYSIS, 2016, 6 (02) :696-708
[2]   Pd-MCM-48: a novel recyclable heterogeneous catalyst for chemo- and regioselective hydrogenation of olefins and coupling reactions [J].
Banerjee, Subhash ;
Balasanthiran, Vagulejan ;
Koodali, Ranjit T. ;
Sereda, Grigoriy A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (19) :4316-4321
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   TANDEM DIAZOTIZATION HECK REACTIONS - A GENERAL-SYNTHESIS OF SUBSTITUTED STYRENES FROM ANILINES [J].
BELLER, M ;
FISCHER, H ;
KUHLEIN, K .
TETRAHEDRON LETTERS, 1994, 35 (47) :8773-8776
[5]   Asymmetric catalysis .108. Copper catalysts with optically active ligands in the enantioselective Meerwein arylation of activated olefins [J].
Brunner, H ;
Bluchel, C ;
Doyle, MP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 541 (1-2) :89-95
[6]   PALLADIUM CATALYZED VINYLATION OF ENOL TRIFLATES [J].
CACCHI, S ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1984, 25 (21) :2271-2274
[7]   Site-selective modification of peptides using rhodium and palladium catalysis: complementary electrophilic and nucleophilic arylation [J].
Chapman, Christopher J. ;
Matsuno, Ai ;
Frost, Christopher G. ;
Willis, Michael C. .
CHEMICAL COMMUNICATIONS, 2007, (38) :3903-3905
[8]   FORMATION OF PHENYLDIIMIDE AND PHENYL RADICAL BY HETEROLYSIS OF N-PHENYL-N]-BENZOYLDIIMIDE [J].
COHEN, SG ;
NICHOLSO.J .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1162-&
[9]   FORMATION OF PHENYL RADICAL BY HETEROLYSIS OF N-PHENYL-N]-BENZOYLDIIMIDE [J].
COHEN, SG ;
NICHOLSON, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3892-&
[10]   The asymmetric intramolecular Heck reaction in natural product total synthesis [J].
Dounay, AB ;
Overman, LE .
CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963