112655-08-0

Upstream product

• 112655-07-9 Carbonic acid (E)-4-methoxycarbonyloxy-5-phenyl-pent-2-enyl ester methyl ester 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 627-41-8 propargyl alcohol methyl ether 
• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 
• 74-88-4 methyl iodide 
• 14371-10-9 (E)-3-phenylpropenal 
• 55894-16-1 (2-methoxyethyl)triphenylphosphonium bromide 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 82859-39-0 trans-cinnamyl iodide 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 1476-07-9 (E)-(3-ethoxy-1-propen-1-yl)benzene 
• 14289-95-3 (E)-(3-isopropoxyprop-1-en-1-yl)benzene 

Downstream Products

• 52692-50-9 ε-methoxypentylbenzene 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 

Relevant academic research and scientific papers

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Oxidative cleavage of allyl ethers by an oxoammonium salt

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.

Nickel-catalyzed allylic substitution of simple alkenes

This report describes a nickel-catalyzed allylic substitution process of simple alkenes whereby an important structural motif, a 1,4-diene, was prepared. The key to success is the use of an appropriate nickel-phosphine complex and a stoichiometric amount of silyl triflate. Reactions of 1-alkyl-substituted alkenes consistently provided 1,1-disubstituted alkenes with high selectivity. Insight into the reaction mechanism as well as miscellaneous application of the developed catalytic process is also documented.

Palladium-catalyzed reactions of 3-substituted methylenecyclopropanes

Pd-catalyzed reactions of 3-substituted methylenecyclopropanes (MCPs), in which the substituents can be either hydroxymethyl or formyl, have been thoroughly investigated in the presence or absence of an acid source. It was found that the Pd-catalyzed reactions of methylenecyclopropylcarbinols (Z)-1 in the presence of acetic acid, acetic acid 2-methylene-but-3-enyl esters 4 can be formed in moderate yields. It was also found that Pd alone can catalyze the isomerization of methylenecyclopropylcarbinols (E)-1 in the absence of an acid source to form pent-4-enals 3. The Pd-catalyzed reactions of methylenecyclopropanecarbaldehydes 5 were also carried out in the presence of acetic acid. It was found that when (E)-5 was used as the substrate, the isomerized product, penta-2,4-dienal 6, could be obtained in good to high yields, whereas the use of (Z)-5 gave 2-(3-formylpenta-2,4-dienylidene) cyclopropanecarbaldehyde 7 in moderate to good yields. Plausible mechanisms for all these transformations have been discussed on the basis of the obtained results and control experiments. Copyright

Nickel-catalyzed allylic substitution of simple alkenes

Nickel-catalyzed intermolecular allylic substitution of simple alkenes (ethylene and alpha olefins) is described. This method is the first catalytic intermolecular process for direct allylation of nonconjugated, nonstrained simple alkenes. Catalyst loadings as low as 2.5 mol % Ni afford the desired product in high yield in both gram-scale and smaller scale coupling reactions.

Synthesis of N-protected allylic amines from allyl ethers

A synthetic method for N-protected allylic amines from allyl ethers using chlorosulfonyl isocyanate (CSI) is presented. The reaction of 4-phenylbut-2-enyl methyl ether (1i) with CSI afforded methyl N-(1-benzylallyl)carbamate (2i) and methyl N-(4-phenylbut

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.

Ionic Photodissociation of Polyenes via a Highly Polarized Singlet Excited State

Several polyene acetates and polyene methyl ether were prepared.Upon direct excitation these polyenes undergo ionic photodissociation from their singlet excited states.Triplet-sensitization experiments on these polyenes revealed that the ionic photodissociation process is restricted to singlet excited states.The rationale put forward is that the polyene chromophore undergoes charge separation/polarization in the singlet excited state, which leads to ionic photodissociation.