114444-87-0

Upstream product

• 80674-45-9 threo-2-tert-Butyl-3-hydroxy-5-phenyl-(E)-4-pentensaeure 
• 100-42-5 styrene 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 917-64-6 methyl magnesium iodide 
• 142039-27-8 2-Methyl-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-[1,3]dithiolane 
• 80674-45-9 erythro-2-tert-Butyl-3-hydroxy-5-phenyl-(E)-4-pentensaeure 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 904319-03-5 3,3-dimethyl-1-buten-2-yl O,O-diphenyl phosphate 
• 630-19-3 pivalaldehyde 
• 91861-48-2 Tributyl-((E)-3-phenyl-allyl)-phosphonium; bromide 
• 38633-40-8 (E)-cinnamyltriphenylphosphonium bromide 
• 201852-49-5 potassium (E)-trifluoro(styryl)borate 
• 300-57-2 allylbenzene 
• 1037197-66-2 C₁₆H₁₄N₄O₂S 

Relevant academic research and scientific papers

Palladium-catalyzed elimination reaction of acyclic (E)-allylic acetates: The stereochemistry elucidated by syn-effect

The stereochemistry of the elimination reaction of acyclic (E)-allylic acetates into the corresponding 1,3-dienes catalyzed by palladium in the presence of a base was investigated. The Z/E ratios of the resulting 1,3-dienes varied with the δ-substituents of the starting allylic acetates. This phenomenon was discussed based on the concept of a syn-effect, which is most primarily rationalized by a σ → π* interaction. Copyright

Palladium-catalyzed cross-coupling of vinylic tellurides and potassium vinyltrifluoroborate salt: synthesis of 1,3-dienes

Here we report an ultrasound-assisted synthesis of stereodefined 1,3-dienes by Suzuki-Miyaura cross-coupling reactions of vinylic tellurides and potassium β-styryl trifluoroborate salt.

Catalytic amide base system generatedin situfor 1,3-diene formation from allylbenzenes and carbonyls

The amide base generatedin situfrom tetramethylammonium fluoride and N(TMS)3catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role oftransβ-methyl stilbenes in product formation is also elucidated.

Julia-Kocienski reaction-based 1,3-diene synthesis: Aldehyde-dependent (E, E/E, Z)-selectivity

A new modification of Julia-Kocienski olefination reaction based on the use of cation-specific chelating agents that yields 1,3-dienes with predictable (E/Z)-selectivity on newly created double bond was developed. The influence of the aldehyde structure on reaction (E/Z) selectivity is discussed and rationalized.

Palladium-tetraphosphine complex catalysed heck reaction of vinyl bromides with alkenes: A powerful access to conjugated dienes

A wide variety of 1,3-dienes have been prepared by the Heck vinylation of vinyl bromides using [Pd(η3-C3H5)Cl] 2/cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino)methyl] cyclopentane (Tedicyp) as the catalyst precursor. Both α- and β-substituted vinyl bromides undergo the Heck reaction with functionalised alkenes such as acrylates, enones, styrenes or a vinyl sulfone, and also with nonfunctionalised alkenes such as dec-1-ene, leading stereoselectively, in most cases, to the corresponding E- or E,E-1,3-dienes in good yields. Furthermore, this catalyst can be used at low loading for several reactions. Georg Thieme Verlag Stuttgart.

Heck coupling with nonactivated alkenyl tosylates and phosphates: Examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates

(Chemical Equation Presented) What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron-deficient olefins. An unexpected 1,2-migration of the alkenyl Pd II intermediates (see Scheme) leads to the isomerized Heck coupling product.

Heck reaction of vinyl bromides with alkenes in the presence of a tetraphosphine/palladium catalyst

Through the use of [PdCl(C3H5)]2- cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of vinyl bromides undergo Heck reaction with a wide variety of alkenes leading selectively to the corresponding 1,3-dienes in good yields. Furthermore, it can be used at low loading even for reactions of sterically hindered vinyl bromides.

Stille couplings catalytic in tin: The "Sn-O" approach

A one-pot tandem Pd-catalyzed hydrostannylation/Stille coupling protocol for the stereoselective generation of vinyltins and their subsequent union, employing only catalytic amounts of tin, is described. By recycling the organotin halide Stille byproduct back to organotin hydride, a hydrostannylation/cross-coupling sequence can be carried out with catalytic amounts of tin. Such a process is most effective with Me3SnCl serving as the tin source. This protocol allows a 94% reduction of the tin requirement, while maintaining good yields (up to 90%) for a variety of Stille products. Furthermore, since one cycle requires the tin to undergo at least four transformations, each moiety of trialkyltin is experiencing a minimum of 60 reactions over the course of the hydrostannylation/Stille, sequence.

Microwave-assisted one-pot hydrostannylation/Stille couplings.

In a fraction of the time required by conventional methods, microwave-accelerated one-pot hydrostannylation/Stille coupling allows 1-alkynes to be efficiently transformed into 1,3-dienes or styrenes.