Palladium-Catalyzed Decarbonylative Heck Coupling of Aromatic Carboxylic Acids with Terminal Alkenes

2020 ◽  
Vol 22 (18) ◽  
pp. 7123-7128
Author(s):  
Wenqing Yu ◽  
Long Liu ◽  
Tianzeng Huang ◽  
Xiangbing Zhou ◽  
Tieqiao Chen
Keyword(s):  
Carboxylic Acids ◽  
Heck Coupling ◽  
Aromatic Carboxylic Acids ◽  
Terminal Alkenes ◽  
Palladium Catalyzed

ChemInform Abstract: “Ligand-Free” Palladium-Catalyzed Direct C-H Bond Oxidative Acyloxylation of 2-Arylpyridines with Aromatic Carboxylic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (35) ◽  
pp. no-no
Author(s):  
Chao-Jun Hu ◽  
Xiao-Hong Zhang ◽  
Qiu-Ping Ding ◽  
Ting Lv ◽  
Shao-Peng Ge ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids ◽  
Ligand Free ◽  
Palladium Catalyzed

Palladium-catalyzed decarboxylative cyanation of aromatic carboxylic acids using [13C] and [14C]-KCN

2015 ◽  
Vol 58 (11-12) ◽  
pp. 425-428 ◽  
Author(s):  
Olivier Loreau ◽  
Dominique Georgin ◽  
Frédéric Taran ◽  
Davide Audisio
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids ◽  
Palladium Catalyzed

An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides

2016 ◽  
Vol 14 (1) ◽  
pp. 246-250 ◽  
Author(s):  
Bing Mu ◽  
Yusheng Wu ◽  
Jingya Li ◽  
Dapeng Zou ◽  
Junbiao Chang ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Carboxylic Acids ◽  
Coupling Reaction ◽  
Aromatic Carboxylic Acids ◽  
Aryl Chlorides ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

An efficient and facile protocol for the synthesis of 3-aryl-imidazo[1,2-a]pyridines was investigated via palladium-catalyzed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids.

An efficient route to regioselective functionalization of benzo[b]thiophenes via palladium-catalyzed decarboxylative Heck coupling reactions: insights from experiment and computation

2016 ◽  
Vol 14 (3) ◽  
pp. 895-904 ◽  
Author(s):  
Daoshan Yang ◽  
Yuxia Liu ◽  
Pengfei Sun ◽  
Ning Zhang ◽  
Wei Wei ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reactions ◽  
Heck Coupling ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
Type Coupling ◽  
Regioselective Functionalization

This study reports the Pd-catalyzed decarboxylative Heck-type coupling of 3-chlorobenzo[b]thiophene-2-carboxylic acids with styrenes.

ChemInform Abstract: Palladium-Catalyzed Synthesis of Aromatic Carboxylic Acids with Silacarboxylic Acids.

ChemInform ◽  
2013 ◽  
Vol 44 (30) ◽  
pp. no-no
Author(s):  
Stig D. Friis ◽  
Thomas L. Andersen ◽  
Troels Skrydstrup
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids ◽  
Palladium Catalyzed

Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling

2018 ◽  
Author(s):  
John A. Gurak ◽  
Keary M. Engle
Keyword(s):  
Functional Groups ◽  
Complex Molecule ◽  
Reductive Elimination ◽  
Heck Coupling ◽  
Deuterium Labeling ◽  
Aryl Iodides ◽  
Terminal Alkenes ◽  
Palladium Catalyzed ◽  
Turn Over

The hydroarylation of alkenes is an attractive approach to construct carbon–carbon (C–C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of unactivated and heteroatom-substituted terminal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications were demonstrated. Deuterium-labeling experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C–H reductive elimination cascade to afford the saturated product and turn over the cycle. <br>

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