Catalytic Direct β-Arylation of Simple Ketones with Aryl Iodides

被引：100

作者：

Huang, Zhongxing ^{[1
]}

Dong, Guangbin ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 47期

关键词：

C-H BONDS; ASYMMETRIC CONJUGATE ADDITION; AEROBIC DEHYDROGENATION; ARYLBORONIC ACIDS; ALPHA-ARYLATION; CARBONYL-COMPOUNDS; CYCLIC ENONES; BORONIC ACIDS; PALLADIUM; ALDEHYDES;

D O I：

10.1021/ja410389a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report a direct beta-arylation of simple ketones with widely available aryl iodides, combining palladium-catalyzed ketone oxidation, aryl-halide activation, and conjugate addition through a single catalytic cycle. Simple cyclic ketones with different ring-sizes, as well as acyclic ketones, can be directly arylated at the beta-position with complete site-selectivity and excellent functional group tolerance.

引用

收藏

页码：17747 / 17750

页数：4

相关论文

共 69 条

[41]

Nelson T. D., 2004, ORG REACTIONS, V63, P265, DOI DOI 10.1002/0471264180.0R063.03

[42] A Three-Component Palladium-Catalyzed Oxidative C-C Coupling Reaction: A Domino Process in Two Dimensions [J].

Nimje, Roshan Y. ;

Leskinen, Mikko V. ;

Pihko, Petri M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (18) :4818-4822

[43] Conjugate addition of aryl boronic acids to enones catalyzed by cationic palladium(II)-phosphane complexes [J].

Nishikata, T ;

Yamamoto, Y ;

Miyaura, N .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (24) :2768-2770

[44] Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Esters Catalyzed by Dicationic Palladium(II)-Chiraphos Complex for Short-Step Synthesis of SmithKline Beecham's Endothelin Receptor Antagonist [J].

Nishikata, Takashi ;

Kiyomura, Shunsuke ;

Yamamoto, Yasunori ;

Miyaura, Norio .

SYNLETT, 2008, (16) :2487-2490

[45] Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated N-acylamides catalyzed by dicationic palladium(II)-(S,S)-chiraphos complex [J].

Nishikata, Takashi ;

Yamamoto, Yasunori ;

Miyaura, Norio .

CHEMISTRY LETTERS, 2007, 36 (12) :1442-1443

[46] Palladium-catalyzed alpha-arylation of ketones [J].

Palucki, M ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (45) :11108-11109

[47] Direct Arylation of Primary and Secondary sp3 C-H Bonds with Diarylhyperiodonium Salts via Pd Catalysis [J].

Pan, Fei ;

Shen, Peng-Xiang ;

Zhang, Li-Sheng ;

Wang, Xin ;

Shi, Zhang-Jie .

ORGANIC LETTERS, 2013, 15 (18) :4758-4761

[48]

Park YW, 1997, B KOR CHEM SOC, V18, P1123

[49] Photoredox Activation for the Direct β-Arylation of Ketones and Aldehydes [J].

Pirnot, Michael T. ;

Rankic, Danica A. ;

Martin, David B. C. ;

MacMillan, David W. C. .

SCIENCE, 2013, 339 (6127) :1593-1596

[50] Aerobic Dehydrogenation of Cyclohexanone to Phenol Catalyzed by Pd(TFA)2/2-Dimethylaminopyridine: Evidence for the Role of Pd Nanoparticles [J].

Pun, Doris ;

Diao, Tianning ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (22) :8213-8221

← 1 2 3 4 5 6 7 →