99142-95-7Relevant academic research and scientific papers
Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions
da Costa, Rafaela G.M.,Farias, Francisco R.L.,Back, Davi,Limberger, Jones
, p. 771 - 775 (2018)
A useful protocol for arylation of the olefin double bond of chalcones to afford tri- and tetra-substituted chalcone derivatives is reported. The protocol begins with the Heck reaction between chalcones and aryl iodides providing β-arylchalcones. This reaction tolerates various functional groups on both rings, as well as deactivated aryl iodides. The products are obtained in moderate to excellent yields and the (E)-β-arylchalcones (E:Z > 96:4) can be isolated via precipitation. Competitive Heck reactions pointed to a significant effect of ring one substituents on the reaction rate, while substituents on ring two have a much smaller effect. To access α,β-diarylchalcones, a sequential bromination-Suzuki cross coupling strategy was applied to the β-arylated compounds which afforded double arylated chalcone derivatives in 60–99% yield over two steps.
Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity
Bangar, Pronnoy G.,Jawalkar, Priyanka R.,Dumbre, Swapnil R.,Raut, Pallavi K.,Patil, Dharmaraj J.,Tv, Neethu,Sudhakaran, Shana,Iyer, Suresh
supporting information, p. 3796 - 3803 (2020/09/01)
Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.
Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium-arylurea complexes
Smith, Matthew R.,Jang, Young Jin,Kim, Jung Yun,Ciufolini, Marco A.
, p. 10139 - 10151 (2013/11/06)
A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)2 with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides).
Hypervalent iodine in synthesis XXX: Palladium-catalyzed reaction of diaryliodonium salts with β-substituted-α, β-enones
Xia, Min,Chen, Zhen Chu
, p. 1281 - 1285 (2007/10/03)
The reaction of diaryliodonium salts with β-substituted-α,β-enones in the presence of a palladium catalyst affords H(β)-substituted products with excellent yields.
Polarized Ketene Dithioacetals. Part 42. Studies on the Reactions of Alkyl and Aryl Grignard Reagents with α-Oxoketene Dithioacetals
Singh, Gurdeep,Purkayastha, Makhan L.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 1289 - 1294 (2007/10/02)
The oxoketene dithioacetals (2a-k) derived from a variety of cyclic and acyclic active methylene ketones undergo 1,2-addition with methylmagnesium iodide to give the alcohol acetals (3a-k) which, on subsequent boron trifluoride-ether catalysed methanolysi
