474661-64-8Relevant academic research and scientific papers
A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission
McAlpine, Neil J.,Wang, Long,Carrow, Brad P.
supporting information, p. 13634 - 13639 (2018/10/24)
Substituted 1,3-dienes are valuable synthetic intermediates used in myriad catalytic transformations, yet modern catalytic methods for their preparation in a highly modular fashion using simple precursors are relatively few. We report here an aerobic boron Heck reaction with cyclobutene that forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic acids, rather than typical Heck products (i.e., substituted cyclobutenes). Experimental and computational mechanistic data support a pericyclic mechanism for C-C bond cleavage that enables the cycloalkene to circumvent established limitations associated with diene reagents in Heck-type reactions.
Scope and limitations of 1,3,5-hexatriene derivatives in regioselective cobalt-catalyzed reactions
Schmidt, Anastasia,Hilt, Gerhard
supporting information, p. 2708 - 2711 (2013/07/26)
Applications of 1,3,5-hexatriene derivatives in atom-economic cobalt-catalyzed transformations, such as the Diels-Alder reaction with alkynes, the 1,4-hydrovinylation reaction with terminal alkenes, and the 1,4-hydrohexatrienylation reaction, are investigated. In all cases, regioselective transformations were found to generate cyclic derivatives such as stilbenes or acyclic products with a high control of the double bond geometry in the skipped trienes derived from the 1,4-hydrovinylation process or the tetraenes generated in the so far unprecedented 1,4-hydrohexatrienylation reaction.
