1322750-02-6Relevant articles and documents
A Sustainable, User-Friendly Protocol for the Pd-Free Sonogashira Coupling Reaction
Liori, Aggeliki A.,Stamatopoulos, Ioannis K.,Papastavrou, Argyro T.,Pinaka, Afroditi,Vougioukalakis, Georgios C.
, p. 6134 - 6139 (2018)
We herein present a new catalytic system for the palladium-free Sonogashira coupling reaction. The catalytically active moiety is formed in situ, in a straightforward and user-friendly manner, by combining a widely available low-cost copper salt and an N-
Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides
Hajipour, Abdol R.,Malek, Shaghayegh Sadeghi
, (2021/04/23)
Aryl chlorides are one of the most stable and available electrophiles, however, their coupling with nucleophiles remains a challenge in organic synthesis. Herein, we prepared a Cobalt-NHC (N-Heterocyclic carbene) complex anchored on magnetic chitosan nanoparticles and assayed its catalytic activity for the reactions of substituted phenylboronic acid and also phenlacetylene with derivatives of aryl chlorides. These reactions are of great importance since they are employed for the synthesis of unsymmetrical diarylethynes and biphenyls, which belong to a prime class of building blocks. The synthesized nanocatalyst was found to be highly efficient in Suzuki and Sonogashira coupling in terms of their activity and recyclability in polyethylene glycol (PEG) as a green reaction media under conditions of temperatures (70 and 100 °C) and Co loading (3 and 6 mol%). To the best of our knowledge, this is the first attempt of using cobalt-NHC complex for catalyzing the abovementioned reactions. Moreover, replacing the earth-abundant Cobalt-based catalyst as an alternative to high cost palladium make this approach promising from sustainable chemistry view.
Nickel-catalyzed oxidative decarboxylative coupling reactions between alkynyl carboxylic acids and arylboronic acids
Lee, Ju-Hyeon,Raja, Gabriel Charles Edwin,Son, Yujeong,Jang, Jisun,Kim, Jimin,Lee, Sunwoo
, p. 4824 - 4828 (2016/10/05)
Nickel-catalyzed decarboxylative coupling reactions between aryl alkynyl carboxylic acids and arylboronic acids were developed. When aryl alkynyl carboxylic acids were reacted with arylboronic acids in the presence of NiCl2(10?mol?%), 2,2′-bipy
One-pot synthesis of unsymmetrical diarylacetylenes via Sonogashira/deacetonation/Sonogashira cross-coupling of two different aryl chlorides with 2-methyl-3-butyn-2-ol
Xu, Kai,Sun, Suyan,Zhang, Guodong,Yang, Fan,Wu, Yangjie
, p. 32643 - 32646 (2014/08/18)
With the assistance of PdCl2/X-Phos as the catalyst system, a green and efficient protocol for one-pot Sonogashira/Deacetonation/Sonogashira coupling reaction of two different aryl chlorides with 2-methyl-3-butyn-2-ol was developed, affording various unsymmetrical diarylacetylenes in mostly moderate to excellent yields. Note that the cheap and economically available aryl chlorides and 2-methyl-3-butyn-2-ol as the starting materials could be added to the catalyst system directly and simultaneously. Moreover, this tandem reaction could tolerate substrates bearing one or even two ortho-sterically hindered groups and was also applicable to the synthesis of symmetrical diarylacetylenes. In addition, the competitive reaction was performed and a possible mechanism was also proposed. This journal is the Partner Organisations 2014.
Phosphane-free copper-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl halides under aerobic conditions
Pan, Delin,Zhang, Chun,Ding, Shengtao,Jiao, Ning
supporting information; experimental part, p. 4751 - 4755 (2011/10/08)
A phosphane-free copper-catalyzed decarboxylative cross-coupling reaction of alkynyl carboxylic acids with aryl halides was developed. CuBr (1-5 mol-%) was used as a catalyst in the presence of a β-diketone ligand in air. The reactions of aryl iodides wer
Ligand-free copper oxide nanoparticle-catalyzed sonogashira coupling reaction
Yuan, Yu,Zhu, Haitao,Zhao, Dongbo,Zhang, Li
experimental part, p. 1792 - 1798 (2011/07/08)
The catalytic Sonogashira coupling reaction of terminal alkynes and aryl halides is developed using copper(II) oxide nanoparticles as catalyst in dimethyl sulfoxide. The procedure is experimentally simple, general, efficient, and free from addition of ext
