211322-72-4Relevant academic research and scientific papers
Direct dichlorovinylation of nitriles with trichloroethylene under phase-transfer catalysis conditions
Jończyk, Andrzej,Gierczak, Agnieszka H.
, p. 962 - 964 (1998)
Reaction of trichloroethylene with nitriles 1a-k, carried out in the presence of 50% aqueous sodium hydroxide and tetrabutylammonium hydrogen sulfate as a phase-transfer catalyst, in diethyl ether at 5-10°C affords dichlorovinyl derivatives 2a-k in good yields. Deprotection of the latent carbonyl group in aminonitrile 1f results in the formation of dichlorovinyl ketone 5.
E - Z isomerization in Suzuki cross-couplings of haloenones: Ligand effects and evidence for a separate catalytic cycle
Chehal, Navneet K.,Budzelaar, Peter H. M.,Hultin, Philip G.
supporting information, p. 1134 - 1143 (2018/02/22)
Suzuki cross-coupling of haloalkenes is generally assumed to occur with retention of the alkene stereochemistry. While studying Suzuki cross-couplings on E-1,2-dichlorovinyl phenyl ketone, we were surprised to observe extensive isomerization. More surprisingly, the ligand employed strongly influenced the degree of isomerization: DPEphos and Xantphos led to 96% isomerized cross-coupled product whereas reactions in the absence of a phosphine ligand, or reactions employing t-BuXantphos, gave 94% retention of stereochemistry. While E-Z isomerization in Pd-catalyzed vinylic couplings has previously been attributed to events within the cross-coupling catalytic cycle, we present experimental and computational evidence for a separate Pd-catalyzed isomerization process in these reactions.
