Functionalized styrene synthesis via palladium-catalyzed C-C cleavage of aryl ketones

被引:5
作者
Zhang, Xu [1 ]
Wang, Zhen-Yu [1 ]
Wang, Xing [2 ]
Xu, Hui [2 ]
Dai, Hui-Xiong [1 ,2 ,3 ]
机构
[1] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China
[2] Univ Chinese Acad Sci, Chinese Acad Sci Key Lab Receptor Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[3] Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
关键词
Styrene; Ligand-promoted; C-C cleavage; Orthogonal Suzuki-Miyaura coupling; CROSS-COUPLING REACTIONS; SINGLE BOND-CLEAVAGE; HECK REACTION; DIRECTED CLEAVAGE; VINYLATION; ALKENES; DIFUNCTIONALIZATION; PROTOCOL; HALIDES; DESIGN;
D O I
10.1016/j.tetlet.2022.153721
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C-C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki-Miyaura cou-pling demonstrated the synthetic practicability.(c) 2022 Elsevier Ltd. All rights reserved.
引用
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页数:4
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共 68 条
[1]   Carbonyl-Olefin Metathesis [J].
Albright, Haley ;
Davis, Ashlee J. ;
Gomez-Lopez, Jessica L. ;
Vonesh, Hannah L. ;
Quach, Phong K. ;
Lambert, Tristan H. ;
Schindler, Corinna S. .
CHEMICAL REVIEWS, 2021, 121 (15) :9359-9406
[2]   Palladium-Catalyzed Enantioselective Narasaka-Heck Reaction/Direct C-H Alkylation of Arenes: Iminoarylation of Alkenes [J].
Bao, Xu ;
Wang, Qian ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) :9577-9581
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   Thermolyses of O-phenyl oxime ethers.: A new source of iminyl radicals and a new source of aryloxyl radicals [J].
Blake, JA ;
Pratt, DA ;
Lin, SQ ;
Walton, JC ;
Mulder, P ;
Ingold, KU .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3112-3120
[5]   The modern interpretation of the Wittig reaction mechanism [J].
Byrne, Peter A. ;
Gilheany, Declan G. .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (16) :6670-6696
[6]   Palladium(0)-Catalyzed Iminohalogenation of Alkenes: Synthesis of 2-Halomethyl Dihydropyrroles and Mechanistic Insights into the Alkyl Halide Bond Formation [J].
Chen, Chen ;
Hou, Longlei ;
Cheng, Mian ;
Su, Jianhua ;
Tong, Xiaofeng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (10) :3092-3096
[7]   Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].
Chen, Feng ;
Wang, Teng ;
Jiao, Ning .
CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661
[8]   Synthesis of 1-azaazulenes from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by palladium-catalyzed cyclization and oxidation [J].
Chiba, S ;
Kitamura, M ;
Saku, O ;
Narasaka, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (04) :785-796
[9]   Chemicals from Alkynes with Palladium Catalysts [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2014, 114 (03) :1783-1826
[10]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923