7564-63-8Relevant articles and documents
Dubondin et al.
, p. 454 (1977)
Pd-Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid
Gao, Yang,Ou, Yang,Goo?en, Lukas J.
supporting information, p. 8709 - 8712 (2019/06/17)
Acrylic acid is presented as an inexpensive, non-volatile vinylating agent in a palladium-catalyzed decarboxylative vinylation of aryl halides. The reaction proceeds through a Heck reaction of acrylic acid, immediately followed by protodecarboxylation of the cinnamic acid intermediate. The use of the carboxylate group as a deciduous directing group ensures high selectivity for monoarylated products. The vinylation process is generally applicable to diversely substituted substrates. Its utility is shown by the synthesis of drug-like molecules and the gram-scale preparation of key intermediates in drug synthesis.
Vinylation of aryl bromides using an inexpensive vinylpolysiloxane
Denmark, Scott E.,Butler, Christopher R.
, p. 63 - 66 (2007/10/03)
(Chemical Equation Presented) A mild and general method for the palladium-catalyzed vinylation of aryl bromides has been developed. The use of tetrabutylammonium fluoride (TBAF) as the activator and an inexpensive and nontoxic vinyl donor, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane (D4V, 1), allows for a general and high-yielding preparation of substituted styrenes.
Forbidden reactions, II. - The disrotatory cyclobutene ringopening
Roth, Wolfgang R.,Rekowski, Volker,Boerner, Sabine,Quast, Michael
, p. 409 - 430 (2007/10/03)
The energy profiles for the con- and disrotatory opening of benzocyclobutene, methylenecyclobutene, and cyclobutene derivatives were established by NO and oxygen trapping. The enthalpy for the transition states for the "forbidden" reactions proofed to be identical with the heat of formation of the orthogonal diradicals derived by geometrical isomerization of the dienes formed in these reactions. These diradicals describe very well the activation barriers observed for the disrotatory opening of bicyclic cyclobutenes ([3.2.0] and [2.2.0] systems), but not for bicyclo[2.1.0]pent-2-ene, indicating here a truly forbidden reaction. VCH Verlagsgesellschaft mbH, 1996.