87212-81-5Relevant articles and documents
Illuminatinganti-hydrozirconation: controlled geometric isomerization of an organometallic species
Gilmour, Ryan,Hostmann, Theresa,Nevesely, Tomá?
, p. 10643 - 10648 (2021/08/20)
A general strategy to enable the formalanti-hydrozirconation of arylacetylenes is reported that mergescis-hydrometallation using the Schwartz Reagent (Cp2ZrHCl) with a subsequent light-mediated geometric isomerization atλ= 400 nm. Mechanistic delineation of thecontra-thermodynamic isomerization step indicates that a minor reaction product functions as an efficientin situgenerated photocatalyst. Coupling of theE-vinyl zirconium species with an alkyne unit generates a conjugated diene: this has been leveraged as a selective energy transfer catalyst to enableE→Zisomerization of an organometallic species. Through anUmpolungmetal-halogen exchange process (Cl, Br, I), synthetically useful vinyl halides can be generated (up toZ?:?E= 90?:?10). This enabling platform provides a strategy to access nucleophilic and electrophilic alkene fragments in both geometric forms from simple arylacetylenes.
Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions
Soengas, Raquel G.,Silva, Vera L. M.,Pinto, Joana,Rodríguez-Solla, Humberto,Silva, Artur M. S.
, p. 99 - 107 (2016/01/26)
We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.
H-β-zeolite catalyzed synthesis of β-bromostyrenes from styrene bromohydrins
Pappula, Venkatanarayana,Donthiri, Ramachandra Reddy,Darapaneni, Chandra Mohan,Subbarayappa, Adimurthy
supporting information, p. 1793 - 1795 (2014/03/21)
Synthesis of β-bromostyrenes from styrene bromohydrins using H-β-zeolite as catalyst under moderate conditions is reported. The catalyst could be regenerated and reused up to three consecutive cycles.
Ionic liquid-promoted stereoselective synthesis of (Z)-vinyl bromides by [bmIm]OH under organic solvent-free conditions: A green approach
Ranu, Brindaban C.,Banerjee, Subhash,Gupta, Jhinuk
, p. 2869 - 2876 (2008/02/12)
A simple and easily accessible ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([bmIm]OH), has been demonstrated as an efficient promoter and reaction medium for the highly stereoselective synthesis of (Z)-vinyl bromides by the debrominative decraboxylation of dibrominated α,β-unsaturated carboxylic acids in high yields. The reaction does not require either a conventional base or an organic solvent. Copyright Taylor & Francis Group, LLC.
A CONVENIENT METHOD FOR THE CONVERSION OF trans to cis-CINNAMIC ACIDS
Galamb, Vilmos,Alper, Howard
, p. 2965 - 2968 (2007/10/02)
trans-Cinnamic acids react in sequence with bromine, base, and carbon monoxide to give cis-acids in reasonable yields.
