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

被引：21

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 50 条

[31] Elucidating the mechanism and origin of diastereoselectivity in scandium-catalyzed β-C(sp3)-H activation and transformation of an aliphatic aldimine
Zhang, Yiran
Wang, Yang
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4391 - 4401
[32] Rh(III)-Catalyzed Hydroarylation of Alkyne MIDA Boronates via C-H Activation of Indole Derivatives
Fei, Xiao
Li, Chunpu
Yu, Xinhong
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6840 - 6850
[33] Iridium-Catalyzed Enantioselective Hydroarylation of Alkenes through C-H bond Activation: Experiment and Computation
Shinde, Valmik S.
Mane, Manoj V.
Cavallo, Luigi
Rueping, Magnus
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (37) : 8308 - 8313
[34] Cobalt-Catalyzed Hydroarylation of Alkynes through Chelation-Assisted C-H Bond Activation
Gao, Ke
Lee, Pin-Sheng
Fujita, Takeshi
Yoshikai, Naohiko
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (35) : 12249 - 12251
[35] Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation
Liu, Yan-Hua
Xie, Pei-Pei
Liu, Lei
Fan, Jun
Zhang, Zhuo-Zhuo
Hong, Xin
Shi, Bing-Feng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (45) : 19112 - 19120
[36] Mechanistic Study of Manganese-Catalyzed C-H Bond Functionalizations: Factors Controlling the Competition between Hydroarylation and Cyclization
Ma, Xiaoxiao
Dang, Yanfeng
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 1916 - 1924
[37] Palladium(II)-Catalyzed Tandem Cyclization/C-H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
Xia, Xiao-Feng
Wang, Ning
Zhang, Lu-Lu
Song, Xian-Rong
Liu, Xue-Yuan
Liang, Yong-Min
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9163 - 9170
[38] Palladium-catalyzed tandem cyclization of bromoenynes through aromatic C-H bond functionalization
Ohno, H
Yamamoto, M
Iuchi, M
Tanaka, T
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (32) : 5103 - 5106
[39] Ni(ii)-catalyzed C-H hydroarylation of diarylacetylenes with imidazolium salts
Wang, Tianbao
Zheng, Xuesong
Zheng, Qinze
Zhou, Fulin
Wang, Linhua
Gao, Ge
CHEMICAL COMMUNICATIONS, 2022, 58 (16) : 2730 - 2733
[40] DFT Case Study on the Comparison of Ruthenium-Catalyzed C-H Allylation, C-H Alkenylation, and Hydroarylation
Zhang, Lei
Wang, Ling-Ling
Fang, De-Cai
ACS OMEGA, 2022, 7 (07): : 6133 - 6141

← 1 2 3 4 5 →