18685-02-4Relevant academic research and scientific papers
The effect of vicinyl olefinic halogens on cross-coupling reactions using Pd(0) catalysis
Organ, Michael G.,Ghasemi, Haleh,Valente, Cory
, p. 9453 - 9461 (2004)
(trans) 1-Chloro-2-iodoethylene (3), (trans) 1-bromo-2-iodoethylene (4), (trans) 1,2-diiodoethylene (5) and (cis and trans) 1,2-dibromoethylene (11) were reacted under Suzuki, Sonogashira and Negishi cross-coupling conditions using Pd catalysis to obtain mono coupled products. Only olefin template 3 provided the desired coupling products reliably under all reaction conditions. Compound 5 did not provide cross coupled products under any of the reaction conditions used. The Negishi reaction was the only one that worked for templates 4 and 11. Studies indicate that oxidative addition of the most reactive carbon-halogen bond to Pd(0) is followed by elimination of the second halide, when the second halide is a bromide or an iodide. This happens to a much lesser degree when the second halogen is a chloride. Graphical Abstract.
A very simple synthesis of chloroalkenes and chlorodienes by selective Suzuki couplings of 1,1- and 1,2-dichloroethylene
Barluenga, Jose,Moriel, Patricia,Aznar, Fernando,Valdes, Carlos
, p. 347 - 353 (2007/10/03)
Chloroalkenes, important building blocks for cross-coupling reactions, are prepared in one step by the Suzuki reaction of 1,1-dichloroethylene and 1,2-dichloroethylene with alkenyl- and arylboronic acids. Under the proper reaction conditions, it is possible to obtain the monocoupling reaction to provide the corresponding chloroalkenes with good yields. This method represents an excellent route for the preparation of chloroalkenes and chlorodienes from commercially available starting materials.
Stereoselective synthesis of Z alkenyl halides via Julia olefination
Lebrun, Marie-Eve,Le Marquand, Paul,Berthelette, Carl
, p. 2009 - 2013 (2007/10/03)
Julia olefination between α-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereoselectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.
Use of InCl3 as a cocatalyst and a Cl2Pd(DPEphos)- P(2-Furyl)3 catalyst system for one-pot hydrometalation-cross- coupling and carbometalation-cross-coupling tandem processes
Qian, Mingxing,Huang, Zhihong,Negishi, Ei-Ichi
, p. 1531 - 1534 (2007/10/03)
One-pot conversion of alkynes to regio- and stereodefined alkenylmetals containing Al and Zr via hydrometalation or carbometalation followed by their Pd-catalyzed cross-coupling with (E)-ICH=CHBr or (E)-ICH=CHCl proceeds cleanly and selectively to give the corresponding 1-halo1,3-dienes in excellent yields using a catalyst system consisting of Cl2Pd(DPEphos), DIBAL-H, and TFP (catalyst A) with InCl3 as a cocatalyst.
