17697-66-4

Upstream product

• 62072-25-7 (E)-2-phenylethenyldicyclohexylborane 
• 870-63-3 prenyl bromide 
• 3017-70-7 2-bromo-3-methylbut-2-ene 
• 536-74-3 phenylacetylene 
• 201852-49-5 potassium (E)-trifluoro(styryl)borate 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 100-42-5 styrene 
• 78-79-5 isoprene 
• 556-82-1 3-methyl-2-buten-1-ol 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Relevant academic research and scientific papers

Preparation of Solid, Substituted Allylic Zinc Reagents and Their Reactions with Electrophiles

The treatment of various allylic chlorides or bromides with zinc dust in the presence of lithium chloride and magnesium pivalate (Mg(OCOtBu)2) in THF affords allylic zinc reagents which, after evaporation of the solvent, produce solid zinc reagents that display excellent thermal stability. These allylic reagents undergo Pd-catalyzed cross-coupling reactions with PEPPSI-IPent, as well as highly regioselective and diastereoselective additions to aryl ketones and aldehydes. Acylation with various acid chlorides regioselectively produces the corresponding homoallylic ketones, with the new C-C bond always being formed on the most hindered carbon of the allylic system.

Dehydrative cross-coupling reactions of allylic alcohols with olefins

The direct dehydrative activation of allylic alcohols and subsequent cross-coupling with alkenes by using palladium catalyst containing a phosphoramidite ligand is described. The activation of the allyl alcohol does not require stoichiometric additives, thus allowing clean, waste-free reactions. The scope is demonstrated by application of the protocol to a series allylic alcohols and vinyl arenes, leading to variety of 1,4-diene products. Based on kinetic studies, a mechanism is proposed that involves a palladium hydride species that activates the allyl alcohol to form the allyl intermediate.

Gaining absolute control of the regiochemistry in the cobalt-catalyzed 1,4-hydrovinylation reaction

The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of

Iron-catalyzed 1,4-addition of α-olefins to dienes

Stereo-and Regiosetective 1,4-Addition A new intermolecular, stereo- and regioselective iron-catalyzed 1,4-addition of α-olefins to 1,3-dlenes using as low as 1 mol % of an iminopyridine-ferrous chloride complex was developed. Importantly, both double bon

Microwave-enhanced cross-coupling of allyl chlorides with vinyltrifluoroborates

The allylation of potassium alkenyltrifluoroborates with allyl chloride via a palladium catalyzed cross-coupling reaction occurs rapidly under microwave irradiation. The allylation reaction produces 1,4-pentadienes in high yields.

Preparation and Reactions of Cyclic and Acyclic Allene Complexes of Zirconocene

The zircone ?-complex of 3-methyl-1,2-butadiene (1,1-dimethylallene) cannot be prepared by simple ligand substitution due to rapid coupling of the initially formed complex with the unreacted allene.This problem was circumvented by generating the allene complex by β-hydrogen elimination from a pre-formed sigma complex.This appears to be a potentially general way to prepare allene complexes of zirconocene if the allene precursor has no cis-vinyl hydrogen.This method has been successfully used to prepare zirconocene complexes of 3-methyl-1,2-cycloheptadiene, 3-methyl-1,2-cyclohexadiene and 4-phenyl-1,2,3-cyclohexatriene.Attempts to prepare a complex of 3-methyl-1,2-cyclopentadiene failed.Selected reactions of two of these cumulene complexes and their coupling products are reported.

Stereospecific Synthesis of 1,4-Dienes by Cross-Coupling of Allyl Halides with Alkenylcopper Intermediates from Alkenyldialkylboranes

Alkenylcopper intermediates, generated from alkenyldialkylborane derivatives of 9-borabicyclononane (9-BBN) and dicyclohexylborane (DCB), undergo stereospecific cross-coupling with allylic halides to yield stereodefined 1,4-dienes.