1076-66-0

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 16215-13-7 trans-Cinnamyl-(4-chlor-phenyl)-sulfon 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 24850-33-7 allyltributylstanane 
• 556-56-9 allyl iodid 
• 106625-70-1 ethyl (1-phenylallyl) carbonate 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 2622-05-1 allylmagnesium bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 106-95-6 allyl bromide 
• 300-57-2 allylbenzene 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 122800-33-3 Acetic acid 4-methylene-2-phenyl-cyclopentyl ester 
• 122800-32-2 Acetic acid 3-methyl-4-phenyl-cyclopent-3-enyl ester 
• 4468-42-2 3-phenylhexane 
• 5078-75-1 1-Phenyl-3-methylcyclopentylbenzen 
• 1560-02-7 trans 1-methyl-2-phenylcyclopentane 
• 63779-64-6 (Z)-1-Phenylhexa-1,5-diene 

Relevant academic research and scientific papers

Iridium-catalyzed enantioselective allyl-allylsilane cross-coupling

An enantioselective allyl-allylsilane cross-coupling involving racemic branched allylic alcohols and allylsilanes is reported. An iridium-(P,olefin) phosphoramidite complex enables the transformation with high regio- and stereoselectivity under operationally simple conditions. The utility of the coupling is demonstrated in a concise catalytic, enantioselective synthesis of a pyrethroid insecticide protrifenbute. Enantioselective allyl-allylsilane cross-coupling between branched racemic allylic alcohols and allylsilanes was developed. An Ir-(P,olefin) catalyst in conjunction with Sc(OTf)3 as the acidic promoter enables the preparation of chiral 1,5-dienes with up to 99 % ee. The described method was successfully applied to the asymmetric synthesis of the pyrethroid insecticide protrifenbute. cod=1,5-cyclooctadiene, Tf=trifluoromethanesulfonyl.

Cobalt- and rhodium-catalyzed cross-coupling reaction of allylic ethers and halides with organometallic reagents

Reactions of 2-alkenyl methyl ether with phenyl, trimethylsilylmethyl, and allyl Grignard reagents in the presence of cobalt(II) complexes are discussed. The success of the reactions heavily depends on the combination of the substrate, ligand, and Grignard reagent. In the reaction of cinnamyl methyl ether, the formation of the linear coupling products predominates over that of the relevant branched products. In the cobalt-catalyzed allylation of allylic ethers, addition of a diphosphine ligand can change the regioselectivity, mainly providing the corresponding branched products. Rhodium complexes catalyze the reactions of allylic ethers and halides with allylmagnesium chloride and allylzinc bromide, respectively, in which the branched coupling product is the major product.

Oxovanadium-induced oxidative desilylation of allylic and benzylic silanes

Cinnamyltrimethylsilane underwent desilylation via one-electron oxidation with VO(OEt)Cl2, which was applied to the cross-coupling with the less oxidizable allylic silanes to give the corresponding 1,5-hexadienes. Chlorination or aromatization

Iridium-Catalyzed Enantioselective Allyl-Allyl Cross-Coupling of Racemic Allylic Alcohols with Allylboronates

Carreira's iridium-(P, olefin) phosphoramidite-based catalytic system that allows asymmetric allyl-allylboronate cross-coupling with high enantioselectivity is reported. This transformation tolerates a large variety of racemic branched allylic alcohols an

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Branched/linear selectivity in palladium-catalyzed allyl-allyl cross-couplings: the role of ligands

Abstract While Pd-catalyzed allyl-allyl cross-couplings in the presence of small-bite-angle bidentate ligands reliably furnish the branched regioisomer with high levels of selectivity, cross-couplings in the presence of large-bite-angle bidentate ligands

Triflimide-catalyzed allyl-allyl cross-coupling: A metal-free allylic alkylation

A highly efficient metal-free intermolecular C(sp3)-C(sp3) allyl-allyl cross-coupling protocol between allyl acetates and allyltrimethylsilanes, which proceeded smoothly in the presence of catalytic triflimide to form 1,5-dienes with good to excellent regioselectivity, has been developed.

Catalytic intermolecular allyl-allyl cross-couplings between alcohols and boronates

We developed catalytic intermolecular C(sp3)-C(sp3) cross-couplings between various allyl alcohols and allyl boronates, which proceeded smoothly in the presence of nickel(0) under mild conditions to form 1,5-dienes with excellent linear- and γ-selectivity; the use of boronates proved to be crucial in terms of reactivity.

Indium(i)-catalyzed alkyl-allyl coupling between ethers and an allylborane

An efficient method for alkyl-allyl cross-coupling between ethers and a 9-BBN-derived allylborane catalyzed by indium(i) triflate has been developed. The allylborane proved to be essential to obtain the desired products in high yields. The reaction displayed good substrate scope including high functional group tolerance. The Royal Society of Chemistry 2011.

Pd-catalyzed enantioselective allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of