Efficient and General Protocol for the Copper-Free Sonogashira Coupling of Aryl Bromides at Room Temperature

2003 ◽  
Vol 5 (22) ◽  
pp. 4191-4194 ◽  
Author(s):  
Arash Soheili ◽  
Jennifer Albaneze-Walker ◽  
Jerry A. Murry ◽  
Peter G. Dormer ◽  
David L. Hughes
Keyword(s):  
Room Temperature ◽  
Sonogashira Coupling ◽  
Aryl Bromides

scholarly journals Efficient and General Protocol for the Copper-Free Sonogashira Coupling of Aryl Bromides at Room Temperature.

ChemInform ◽  
2004 ◽  
Vol 35 (9) ◽  
Author(s):  
Arash Soheili ◽  
Jennifer Albaneze-Walker ◽  
Jerry A. Murry ◽  
Peter G. Dormer ◽  
David L. Hughes
Keyword(s):  
Room Temperature ◽  
Sonogashira Coupling ◽  
Aryl Bromides

ChemInform Abstract: Sonogashira Couplings of Aryl Bromides: Room Temperature, Water Only, No Copper.

ChemInform ◽  
2009 ◽  
Vol 40 (2) ◽  
Author(s):  
Bruce H. Lipshutz ◽  
David W. Chung ◽  
Brian Rich
Keyword(s):  
Room Temperature ◽  
Aryl Bromides ◽  
Temperature Water

A Convenient Procedure for Sonogashira Reactions Using Propyne

Synthesis ◽  
2021 ◽  
Author(s):  
George A. Kraus ◽  
Joshua L Alterman
Keyword(s):  
Room Temperature ◽  
Sonogashira Coupling ◽  
Convenient Procedure ◽  
Aryl Iodides ◽  
Sonogashira Reactions

A modified Sonogashira coupling of aryl iodides and propyne was achieved using only two equivalents of propyne in THF from -78°C to room temperature.

Environmentally Benign Microwave-Assisted Sonogashira Preparation of Aromatic Compounds

2011 ◽  
Vol 695 ◽  
pp. 113-116 ◽  
Author(s):  
Suttikiat Puechmongkol ◽  
Boonchoat Paosawatyanyong ◽  
Worawan Bhanthumnavin
Keyword(s):  
Coupling Reaction ◽  
Environmentally Benign ◽  
Conventional Heating ◽  
Microwave Activation ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Aryl Bromides ◽  
Sonogashira Coupling Reaction ◽  
Type Coupling

An efficient Sonogashira-type coupling reaction of terminal alkynes and aryl bromides by microwave activation with short reaction time under mild conditions are presented. It is illustrated herein that the traditional Sonogashira coupling reaction can be achieved with a much more efficient yet environmentally friendly condition. In contrary to the usually required 10 mol% Pd loading and the use of conventional heating at 60 °C for 24 h in order for a reaction to proceed satisfactorily, with a 100 W microwave activation, the reaction of terminal alkynes with substituted aryl bromides can be achieved with only a 2.5 mol% Pd in 10 min. The yield was improved with microwave irradiation.

Hydrazone-Promoted Sonogashira Coupling Reaction with Aryl Bromides at Low Palladium Loadings

Synlett ◽  
2011 ◽  
Vol 2011 (09) ◽  
pp. 1277-1280 ◽  
Author(s):  
Takashi Mino ◽  
Saori Suzuki ◽  
Kiminori Hirai ◽  
Masami Sakamoto ◽  
Tsutomu Fujita
Keyword(s):  
Coupling Reaction ◽  
Sonogashira Coupling ◽  
Aryl Bromides ◽  
Sonogashira Coupling Reaction

Room Temperature Suzuki Reactions in Aqueous Media under Air by Palladium(II) Complexes with Pyrazole Derived Ligands

2010 ◽  
Vol 63 (2) ◽  
pp. 315 ◽  
Author(s):  
Kai Xu ◽  
Xin-Qi Hao ◽  
Jun-Fang Gong ◽  
Mao-Ping Song ◽  
Yang-Jie Wu
Keyword(s):  
Aqueous Solution ◽  
13C Nmr ◽  
Room Temperature ◽  
Phenylboronic Acid ◽  
Aqueous Media ◽  
Palladium Complexes ◽  
Coupling Reactions ◽  
X Ray ◽  
Suzuki Reactions ◽  
Aryl Bromides

Two new palladium complexes with pyrazole derived ligands 2a–2b have been easily prepared and well characterized by elemental analysis, 1H NMR, 13C NMR, and IR spectra. Their detailed structures are determined by a single-crystal X-ray analysis of 2a. The two compounds were successfully applied to the Suzuki coupling reactions of aryl bromides with phenylboronic acid, in aqueous solution at room temperature under air, giving the desired coupled products in good to excellent yields with catalyst loadings as low as 0.01–0.05 mol-%.

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