Rhodium(III)-Catalyzed Meta-Selective C-H Alkenylation of Phenol Derivatives

被引:39
作者
Mi, Rui-Jie [1 ]
Sun, Yong-Zhen [1 ]
Wang, Jing-Yun [1 ]
Sun, Jing [1 ]
Xu, Zhaoqing [2 ]
Zhou, Ming-Dong [1 ]
机构
[1] Liaoning Shihua Univ, Sch Chem & Mat Sci, Fushun 113001, Peoples R China
[2] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Gansu, Peoples R China
关键词
BOND FUNCTIONALIZATION; DIRECTING GROUP; N BOND; CYCLATIVE CAPTURE; COUPLING REACTION; ACTIVATION; OLEFINATION; TEMPLATE; ARENES; ARYLATION;
D O I
10.1021/acs.orglett.8b01995
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(III)-catalyzed remote meta-selective C-H alkenylation of phenol derivatives has been developed using a traceless organosilicon template as the directing group. This transformation proceeds smoothly with good yields and high meta-selectivities toward a series of phenol and alkene substrates. In addition, this protocol provides an effective strategy for late-stage transformations of various meta-alkenylated aromatic compounds.
引用
收藏
页码:5126 / 5129
页数:4
相关论文
共 74 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   A Nickel-Catalyzed Benzannulation Approach to Aromatic Boronic Esters [J].
Auvinet, Anne-Laure ;
Harrity, Joseph P. A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) :2769-2772
[3]   Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly [J].
Bag, Sukdev ;
Patra, Tuhin ;
Modak, Atanu ;
Deb, Arghya ;
Maity, Soham ;
Dutta, Uttam ;
Dey, Aniruddha ;
Kancherla, Rajesh ;
Maji, Arun ;
Hazra, Avijit ;
Bera, Milan ;
Maiti, Debabrata .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) :11888-11891
[4]   Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination [J].
Bera, Milan ;
Maji, Arun ;
Sahoo, Santosh K. ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (29) :8515-8519
[5]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[6]   Remote Meta-C-H Activation Using a Pyridine-Based Template: Achieving Site-Selectivity via the Recognition of Distance and Geometry [J].
Chu, Ling ;
Shang, Ming ;
Tanaka, Keita ;
Chen, Qinghao ;
Pissarnitski, Natalya ;
Streckfuss, Eric ;
Yu, Jin-Quan .
ACS CENTRAL SCIENCE, 2015, 1 (07) :394-399
[7]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[8]   Introduction to Selective Functionalization of C-H Bonds [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2010, 110 (02) :575-575
[9]  
CUI N, 2017, CHINESE J ORG CHEM, V37, P20, DOI DOI 10.6023/CJOC201607017
[10]   Pd(II)-Catalyzed ortho- or meta-C-H Olefination of Phenol Derivatives [J].
Dai, Hui-Xiong ;
Li, Gang ;
Zhang, Xing-Guo ;
Stepan, Antonia F. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7567-7571