Rhodium-Catalyzed Selective C-H Activation/Olefination of Phenol Carbamates

被引：174

作者：

Gong, Tian-Jun ^{[1
]}

Xiao, Bin ^{[1
,2
]}

Liu, Zhao-Jing ^{[1
]}

Wan, Jian ^{[1
]}

Xu, Jun ^{[1
]}

Luo, Dong-Fen ^{[1
]}

Fu, Yao ^{[1
]}

Liu, Lei ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Joint Lab Green Synthet Chem, Hefei 230026, Peoples R China

[2] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 12期

关键词：

INTERNAL ALKYNES; BOND ACTIVATION; OLEFINATION; FUNCTIONALIZATION; ARENES; ACIDS; COUPLING/CYCLIZATION; ALKENYLATION; TEMPERATURE; DERIVATIVES;

D O I：

10.1021/ol201140q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different reactivity as compared to the Pd-catalyzed ortho-arylation reaction of phenol esters and provides a new approach for the synthesis of ortho-substituted phenols.

引用

页码：3235 / 3237

页数：3

共 50 条

[31] Rhodium-catalyzed oxidative coupling through C-H activation and annulation directed by phosphonamide and phosphinamide groups [J].

Park, Sangjune ;

Seo, Boram ;

Shin, Seohyun ;

Son, Jeong-Yu ;

Lee, Phil Ho .

CHEMICAL COMMUNICATIONS, 2013, 49 (77) :8671-8673

[32] Rhodium(III)-Catalyzed Meta-Selective C-H Alkenylation of Phenol Derivatives [J].

Mi, Rui-Jie ;

Sun, Yong-Zhen ;

Wang, Jing-Yun ;

Sun, Jing ;

Xu, Zhaoqing ;

Zhou, Ming-Dong .

ORGANIC LETTERS, 2018, 20 (17) :5126-5129

[33] Rhodium-Catalyzed Enantioselective Silylation of Cyclopropyl C-H Bonds [J].

Lee, Taegyo ;

Hartwig, John F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) :8723-8727

[34] Rhodium-Catalyzed Directed C-H Amidation of Imidazoheterocycles with Dioxazolones [J].

Samanta, Sadhanendu ;

Mondal, Susmita ;

Ghosh, Debashis ;

Hajra, Alakananda .

ORGANIC LETTERS, 2019, 21 (12) :4905-4909

[35] Rhodium-Catalyzed Directed Sulfenylation of Arene C-H Bonds [J].

Yang, Yaxi ;

Hou, Wei ;

Qin, Lihuai ;

Du, Juanjuan ;

Feng, Huijin ;

Zhou, Bing ;

Li, Yuanchao .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) :416-420

[36] Synthesis of Heterocycles Based on Rhodium-Catalyzed C-H Amination [J].

Takahashi, Keisuke ;

Yamaguchi, Daisuke ;

Ishihara, Jun ;

Hatakeyama, Susumi .

SYNLETT, 2014, 25 (01) :133-137

[37] Rhodium-catalyzed direct C-H bond alkynylation of aryl sulfonamides with bromoalkynes [J].

Hou, Hongcen ;

Zhao, Yongli ;

Pu, Shouzhi ;

Chen, Junmin .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (11) :2948-2953

[38] Rhodium-Catalyzed Alkenyl C-H Activation and Oxidative Coupling with Allylic Alcohols [J].

Yan, Rui ;

Wang, Zhong-Xia .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) :240-247

[39] Functionalization of amino acids and peptides via rhodium-catalyzed C-H activation [J].

Tang, Xiao ;

van der Eycken, Erik V. ;

Song, Liangliang .

CHEMICAL COMMUNICATIONS, 2025,

[40] Rhodium-catalyzed C-H activation and conjugate addition under mild conditions [J].

Yang, Luo ;

Correia, Camille A. ;

Li, Chao-Jun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) :7176-7179

← 1 2 3 4 5 →