22692-80-4Relevant articles and documents
An oxygen-bridged bimetallic [Cu-O-Se] catalyst for Sonogashira cross-coupling
Behera, Pradyota Kumar,Bisoyi, Abinash,Bisoyi, Tanmayee,Choudhury, Prabhupada,Gorantla, Koteswara Rao,Mallik, Bhabani S.,Mohapatra, Manoj,Rout, Laxmidhar,Sahu, Rashmi Ranjan,Sahu, Santosh Kumar
supporting information, p. 1650 - 1657 (2022/02/05)
Most non-palladium catalysts employed in Sonogashira cross-coupling work at high temperatures of 120-140 °C and with well-defined ligands. Palladium-based catalysts with bulky and electron-rich phosphine ligands generally show the best performance for the above-mentioned cross-coupling procedure. Herein, we report a new protocol for Csp-Csp2 Sonogashira cross-coupling between a terminal alkyne and aryl halide using the cheap and commercially available catalyst CuSeO3·2H2O. The title reaction proceeds using a variety of terminal alkynes, affording diaryl or aryl-alkyl acetylenes in high yields under mild conditions in the absence of ligands. Alkyl acetylenes, ethynylsilanes, and alkynols are efficiently coupled with aryl iodides and aryl bromides. The mechanism of the reaction was evaluated using computational DFT studies. To the best of our knowledge, this is the first example of the use of an oxygen-bridged copper-based bimetallic catalyst for Csp-Csp2 Sonogashira cross-coupling reactions under mild conditions. The reaction is palladium-free up to a limit of 0.2 ppm. This journal is
Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents
Li, Qing-Han,Wu, Chuan
supporting information, (2021/08/25)
A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.
Visible-Light-Assisted Cobalt-2-(hydroxyimino)-1-phenylpropan-1-one Complex Catalyzed Pd/Cu-Free Sonogashira–Hagihara Cross-Coupling Reaction
Song, Jin-Yi,Zhou, Xuan,Song, He,Liu, Yang,Zhao, Hong-Yan,Sun, Zhi-Zhong,Chu, Wen-Yi
, p. 758 - 762 (2018/01/27)
An effective and inexpensive strategy for the Co(C9H9NO2)3 catalyzed Sonogashira–Hagihara cross-coupling reaction of aryl bromides containing electron-rich and electron-poor substituents with terminal alkynes wa
Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes
Qian, Liang-Wei,Sun, Mengli,Dong, Jianyu,Xu, Qing,Zhou, Yongbo,Yin, Shuang-Feng
supporting information, p. 6764 - 6769 (2017/07/15)
A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.
A novel silica-supported palladium catalyst for a copper-free Sonogashira coupling reaction
Tyrrell, Elizabeth,Al-Saardi, Ali,Millet, Julien
, p. 487 - 488 (2007/10/03)
3-Aminopropyl functionalised silica gel may be readily transformed into a stable immobilised palladium catalyst. This catalyst was then successfully employed in a series of fast, copper-free Sonogashira coupling reactions. Georg Thieme Verlag Stuttgart.
