Tandem Cyclization/Hydroarylation of α,ω-Dienes Triggered by Scandium-Catalyzed C-H Activation

被引：24

作者：

Tang, Bin ^{[1
]}

Hu, Xiaoyan ^{[1
]}

Liu, Chunli ^{[1
]}

Jiang, Tao ^{[1
]}

Alam, Fakhre ^{[1
]}

Chen, Yanhui ^{[1
]}

机构：

[1] Tianjin Univ Sci & Technol, Coll Chem Engn & Mat Sci, TEDA, 29 13th Ave, Tianjin 300457, Peoples R China

来源：

ACS CATALYSIS | 2019年 / 9卷 / 01期

基金：

中国国家自然科学基金;

关键词：

ring-closure; C-H activation; dienes; hydroarylation; rare earths; BOND ACTIVATION; CASCADE CARBOALUMINATION; NATURAL-PRODUCTS; DIENES; CYCLIZATION/HYDROSILYLATION; ALKYLATION; FUNCTIONALIZATION; CYCLIZATION; COMPLEX; OLEFINS;

D O I：

10.1021/acscatal.8b04713

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A highly regio- and diastereoselective, cyclization/hydroarylation reaction of 1,5- and 1,6-dienes with aromatic ethers and tertiary anilines was established by a cationic 2-picoline-tethered-half-sandwich scandium alkyl catalyst, which constitutes a process for producing a diverse array of cis-1,3-disubstituted arylated and trans-1,2-disubstituted benzylated methylcyclopentane derivatives in one step with 100% atom-efficiency. Furthermore, a mechanism involving a scandium-catalyzed aromatic ortho-C-H activation and alkene-insertion cascade was also proposed.

引用

页码：599 / 604

页数：11

共 51 条

[41] Enantio- and diastereoselective catalytic carboalumination of 1-alkenes and α,ω-dienes with cationic zirconocenes:: Scope and mechanism [J].

Shaughnessy, KH ;

Waymouth, RM .

ORGANOMETALLICS, 1998, 17 (26) :5728-5745

[42] CARBOMETALATION OF ALPHA,OMEGA-DIENES AND OLEFINS CATALYZED BY ZIRCONOCENES [J].

SHAUGHNESSY, KH ;

WAYMOUTH, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5873-5874

[43] ortho-Selective C-H addition of N,N-dimethyl anilines to alkenes by a yttrium catalyst [J].

Song, Guoyong ;

Luo, Gen ;

Oyamada, Juzo ;

Luo, Yi ;

Hou, Zhaomin .

CHEMICAL SCIENCE, 2016, 7 (08) :5265-5270

[44] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation [J].

Song, Guoyong ;

Wang, Fen ;

Li, Xingwei .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3651-3678

[45] C-H bond activation enables the rapid construction and late-stage diversification of functional molecules [J].

Wencel-Delord, Joanna ;

Glorius, Frank .

NATURE CHEMISTRY, 2013, 5 (05) :369-375

[46] Synthetic and mechanistic studies of the cycloisomerization and cyclization/hydrosilylation of functionalized dienes catalyzed by cationic palladium(II) complexes [J].

Widenhoefer, RA .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :905-913

[47] Cyclization/hydrogermylation of functionalized 1,6-dienes catalyzed by cationic palladium complexes [J].

Widenhoefer, RA ;

Vadehra, A ;

Cheruvu, PK .

ORGANOMETALLICS, 1999, 18 (22) :4614-4618

[48] Tandem cyclization/hydrosilylation of functionalized 1,6-dienes catalyzed by a cationic palladium complex [J].

Widenhoefer, RA ;

DeCarli, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3805-3806

[49] C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals [J].

Yamaguchi, Junichiro ;

Yamaguchi, Atsushi D. ;

Itami, Kenichiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :8960-9009

[50] Transition-Metal-Catalyzed Cycloisomerizations of α,ω-Dienes [J].

Yamamoto, Yoshihiko .

CHEMICAL REVIEWS, 2012, 112 (08) :4736-4769

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