Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes

被引：81

作者：

Xu, Hua-Jin ^{[1
]}

Kang, Yan-Shang ^{[1
]}

Shi, Hang ^{[2
]}

Zhang, Ping ^{[1
]}

Chen, You-Ke ^{[1
]}

Zhang, Bing ^{[1
]}

Liu, Zhi-Qiang ^{[1
]}

Zhao, Jing ^{[1
]}

Sun, Wei-Yin ^{[1
]}

Yu, Jin-Quan ^{[2
]}

Lu, Yi ^{[1
]}

机构：

[1] Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Coordinat Chem Inst,Nanjing Natl Lab Microstruct, State Key Lab Coordinat Chem,Sch Chem & Chem Engn, Nanjing 210023, Jiangsu, Peoples R China

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 01期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

BOND FUNCTIONALIZATION; DIRECTING GROUP; ARYLATION; OLEFINATION; BORYLATION; ALKYLATION; LIGAND; ACTIVATION; ARENES; CATALYSIS;

D O I：

10.1021/jacs.8b11038

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rh(III)-catalyzed meta-C-H functionalization reactions are still rare. Herein, we report the first example of Rh(III)-catalyzed meta-C-H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl-disubstituted alkynes to afford synthetically valuable trisubstituted olefins. Propargyl alcohols are also compatible, affording complex allylic alcohols. Notably, transition metal-catalyzed metaalkenylation with alkynes has not been successful with Pd catalysts.

引用

页码：76 / 79

页数：4

共 54 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] 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

[3] Rhodium-Catalyzed meta-C-H Functionalization of Arenes [J].

Bera, Milan ;

Agasti, Soumitra ;

Chowdhury, Rajdip ;

Mondal, Rahul ;

Pal, Debasis ;

Maiti, Debabrata .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (19) :5272-5276

[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] 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

[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 Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[8] Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling [J].

Cruz, Faben A. ;

Chen, Zhiwei ;

Kurtoic, Sarah I. ;

Dong, Vy M. .

CHEMICAL COMMUNICATIONS, 2016, 52 (34) :5836-5839

[9] 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

[10] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

← 1 2 3 4 5 6 →