Sequential Functionalization of meta-C-H and ipso-C-O Bonds of Phenols

被引：82

作者：

Xu, Jiancong ^{[1
,2
]}

Chen, Jingjing ^{[1
,2
]}

Gao, Feng ^{[1
,2
]}

Xie, Shuguang ^{[1
,2
]}

Xu, Xiaohua ^{[1
,2
,3
]}

Jin, Zhong ^{[1
,2
,3
]}

Yu, Jin-Quan ^{[4
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

[3] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

[4] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 05期

关键词：

NICKEL-CATALYZED AMINATION; ARYL 2-PYRIDYL ETHERS; ARENES; ACTIVATION; BORYLATION; OLEFINATION; ARYLATION; LIGAND; ALKYLATION; CLEAVAGE;

D O I：

10.1021/jacs.8b13403

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of a template as a linchpin motif in directed remote C-H functionalization is a versatile yet relatively underexplored strategy. We have developed a template-directed approach to realizing one-pot sequential palladium-catalyzed meta-selective C-H olefination of phenols, and nickel-catalyzed ipso-C-O activation and arylation. Thus, this bifunctional template converts phenols to synthetically useful 1,3-disubstituted arenes.

引用

页码：1903 / 1907

页数：5

共 49 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 concise, total synthesis of the TMC-95A/B proteasome inhibitors [J].

Albrecht, BK ;

Williams, RM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :11949-11954

[3] Template-Assisted meta-C-H Alkylation and Alkenylation of Arenes [J].

Bag, Sukdev ;

Jayarajan, Ramasamy ;

Mondal, Rahul ;

Maiti, Debabrata .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) :3182-3186

[4] 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

[5] 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

[6] BIOMIMETIC CONTROL OF CHEMICAL SELECTIVITY [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (06) :170-177

[7] Agostic interactions in transition metal compounds [J].

Brookhart, Maurice ;

Green, Malcolm L. H. ;

Parkin, Gerard .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (17) :6908-6914

[8] Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol [J].

Cheng, Chen ;

Hartwig, John F. .

SCIENCE, 2014, 343 (6173) :853-857

[9] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[10] 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

← 1 2 3 4 5 →