Palladium-Catalyzed Decarboxylative γ-Olefination of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Vinyl Halides

被引:11
作者
Chang, Chi-Hao [1 ]
Chou, Chih-Ming [1 ]
机构
[1] Natl Univ Kaohsiung, Dept Appl Chem, 700 Kaohsiung Univ Rd, Kaohsiung 81148, Taiwan
关键词
C-H OLEFINATION; ALPHA-OXOCARBOXYLIC ACIDS; CROSS-COUPLING REACTIONS; CARBOXYLIC-ACIDS; CONJUGATED POLYMERS; CINNAMIC-ACIDS; HECK REACTION; ACTIVATION; ARYLATION; FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.8b00486
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This study explores a Pd-catalyzed decarboxylative Heck-type Csp(3)-Csp(2) coupling reaction of 2,5-cyclohexadiene-1-carboxylic acid derivatives with vinyl halides to provide gamma-olefination products. The olefinated 1,3-cyclohexadienes can be further oxidized to produce meta-alkylated stilbene derivatives. Additionally, the conjugated diene products can also undergo a Diels-Alder reaction to produce a bicyclo[2.2.2]octadiene framework.
引用
收藏
页码:1949 / 1952
页数:4
相关论文
共 75 条
[71]   Palladium-Catalyzed Meta-Selective C-H Bond Activation with a Nitrile-Containing Template: Computational Study on Mechanism and Origins of Selectivity [J].
Yang, Yun-Fang ;
Cheng, Gui-Juan ;
Liu, Peng ;
Leow, Dasheng ;
Sun, Tian-Yu ;
Chen, Ping ;
Zhang, Xinhao ;
Yu, Jin-Quan ;
Wu, Yun-Dong ;
Houk, K. N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :344-355
[72]   Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Alkenyl Tosylates for the Synthesis of Enynones [J].
Yu, Subeen ;
Cho, Eunjeong ;
Kim, Jimin ;
Lee, Sunwoo .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20) :11150-11156
[73]  
Zhang J, 2016, NAT CHEM, V8, P1144, DOI [10.1038/NCHEM.2602, 10.1038/nchem.2602]
[74]   Domino-Fluorination-Protodefluorination Enables Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids with Styrene via Photoredox Catalysis [J].
Zhang, Muliang ;
Xi, Junwei ;
Ruzi, Rehanguli ;
Li, Nan ;
Wu, Zhongkai ;
Li, Weipeng ;
Zhu, Chengjian .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18) :9305-9311
[75]   Silver-Catalyzed Double-Decarboxylative Cross-Coupling of α-Keto Acids with Cinnamic Acids in Water: A Strategy for the Preparation of Chalcones [J].
Zhang, Ning ;
Yang, Daoshan ;
Wei, Wei ;
Yuan, Li ;
Nie, Fafa ;
Tian, Laijin ;
Wang, Hua .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) :3258-3263