1,2-Alkylarylation of Activated Alkenes with Two C-H Bonds by Using Visible-Light Catalysis

被引：58

作者：

Zhang, Jia-Ling ^{[1
]}

Liu, Yu ^{[1
]}

Song, Ren-Jie ^{[1
]}

Jiang, Guo-Fang ^{[1
]}

Li, Jin-Heng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China

来源：

SYNLETT | 2014年 / 25卷 / 07期

关键词：

alkylarylation; alkenes; acetonitrile; acetone; visible-light catalysis; oxindoles; ARYL DIAZONIUM SALTS; PHOTOREDOX CATALYSIS; OXINDOLES BEARING; C(SP3)H BOND; FUNCTIONALIZATION; ACRYLAMIDES; CASCADE; PHOTOCATALYSIS; CARBON; ACCESS;

D O I：

10.1055/s-0033-1340956

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new visible-light promoted strategy for the difunctionalization of activated alkenes with two C-H bonds has been developed. In the presence of [Ru(bpy)(3)Cl-2], 4-MeOC6H4N2BF4, Na2CO3 and 36W compact fluorescent light, a variety of N-arylacrylamides underwent the 1,2-alkylarylation reaction with acetonitrile or acetone to give the corresponding functionalized oxindoles in moderate to good yields.

引用

收藏

页码：1031 / 1035

页数：5

相关论文

共 61 条

[1] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[2] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[3] PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES [J].

CANOYELO, H ;

DERONZIER, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06) :1093-1098

[4] PHOTO-OXIDATION OF SOME CARBINOLS BY THE RU(II) POLYPYRIDYL COMPLEX ARYL DIAZONIUM SALT SYSTEM [J].

CANOYELO, H ;

DERONZIER, A .

TETRAHEDRON LETTERS, 1984, 25 (48) :5517-5520

[5] PHOTO-OXIDATION OF TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II) BY PARA-SUBSTITUTED BENZENE DIAZONIUM SALTS IN ACETONITRILE 2-COMPARTMENT PHOTOELECTROCHEMICAL CELL APPLICATIONS [J].

CANOYELO, H ;

DERONZIER, A .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1984, 80 :3011-3019

[6] NEW TYPE OF ANTICONVULSANT - "1-ARYL-3-OXOTETRAHYDROISOQUINOLINES [J].

DEAK, G ;

DODA, M ;

GYORGY, L ;

HAZAI, L ;

STERK, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (11) :1384-1388

[7] Iron-Catalyzed Oxidative Arylmethylation of Activated Alkenes Using a Peroxide as the Methyl Source [J].

Fan, Jian-Hong ;

Zhou, Ming-Bo ;

Liu, Yu ;

Wei, Wen-Ting ;

Ouyang, Xuan-Hui ;

Song, Ren-Jie ;

Li, Jin-Heng .

SYNLETT, 2014, 25 (05) :657-660

[8] Synthesis of 3,3-Disubstituted Oxindoles by Visible-Light-Mediated Radical Reactions of Aryl Diazonium Salts with N-Arylacrylamides [J].

Fu, Weijun ;

Xu, Fengjuan ;

Fu, Yuqin ;

Zhu, Mei ;

Yu, Jiaqi ;

Xu, Chen ;

Zou, Dapeng .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) :12202-12206

[9] Photodecarboxylation of phenylglyoxylic acid:: influence of para-substituents on the triplet state properties [J].

Görner, H ;

Kuhn, HJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (12) :2671-2680

[10] The Photocatalyzed Meerwein Arylation: Classic Reaction of Aryl Diazonium Salts in a New Light [J].

Hari, Durga Prasad ;

Koenig, Burkhard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (18) :4734-4743

← 1 2 3 4 5 6 7 →