89703-87-7

Upstream product

• 934-56-5 trimethyl(phenyl)stannane 
• 21699-64-9 trans-2-phenyl-3-ethenyl oxirane 
• 21040-45-9 Cinnamyl acetate 
• 100-52-7 benzaldehyde 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 99441-44-8 cinnamyl tetrahydropyranyl ether 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 26900-57-2 cinnamyltrimethylstannane 
• 63522-99-6 (E)-3-phenyl-2-propenyltrimethylstannane 
• 1462-75-5 3-phenylpropylmagnesium bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 673-32-5 1-Phenylprop-1-yne 
• 89703-88-8 2-phenyl-1-phenyl-3-buten-1-one 
• 74785-32-3 (E)-cinnamyl(tributyl)tin 

Downstream Products

• 84107-76-6 (3E)-1,4-diphenylbut-3-en-1-ol 
• 5731-95-3 1,2-diphenyl-1,3-butadiene 
• 1403477-84-8 1,2-diphenyl-but-3-en-1-one oxime 
• 37928-17-9 5-methyl-3,4-diphenyl isoxazole 
• 87141-85-3 (1R,2R)-2-Oxiranyl-1,2-diphenyl-ethanol 
• 1221447-22-8 (E)-1,2-diphenyl-but-3-en-1-one oxime 

Relevant academic research and scientific papers

Facile preparation of allylzinc species from allyl bromides and unactivated zinc induced by a catalytic amount of aluminum chloride and their reactions with carbonyl compounds and acetals

The effects of Lewis acids (ZnCl2, AlCl3, BF3, and TiCl4) on the generation of allylzinc species from allyl bromide and unactivated zinc powder in dry tetrahydrofuran (THF) were examined by trapping the organozinc compound with benzaldehyde, that is, Grignard-type allylation of the aldehyde. Among the Lewis acids employed, AlCl3 was found to be the promoter of choice. The allylzinc species preformed in the presence of a catalytic amount of AlCl3 effectively allylated carbonyl compounds. Various aromatic and aliphatic aldehydes as well as ketones were converted into homoallylic alcohols in good to excellent yields. Under the reaction conditions employed, ester, hydroxy, acetal, and aromatic nitro and halide groups were tolerated. In the case of α,β-unsaturated carbonyl compounds, selective 1,2-addition was observed. Substituted allyl bromides such as prenyl, crotyl, cinnamyl, and 2-cyclohexenyl bromides were smoothly converted to the corresponding allylzinc compounds, which reacted with carbonyl compounds to give substituted homoallylic alcohols in excellent yields. The diastereoselectivity in crotylation, cinnamylation, and 2-cyclohexenylation depended upon the structures of both the organic metals and the electrophiles. The origin of the observed selectivity is discussed. The allylation of dimethyl and cyclic acetals accompanied with carbon-oxygen bond cleavage also proceeded in excellent yields provided that two equivalents of AlCl3 was present.

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.

Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.

Palladium-Catalyzed Diastereoselective Synthesis of (Z)-Conjugated Enynyl Homoallylic Alcohols

The diastereoselective synthesis of anti-homoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described. This reaction features a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. In this reaction, Pd(0) functions as a catalyst in two fundamental steps of the tandem sequence: 1) the generation of a borylated π-allylpalladium species from bifunctional conjunctive reagents, inducing umpolung allylation of aldehydes, and 2) C(sp2)?C(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility. (Figure presented.).

Bismuth mediated barbier synthesis of α-homoallylic alcohols via a sigmatropic rearrangement in [bmim][HSO4]

A novel protocol for the Bismuth metal mediated regioselctive crotylation of aldehydes yielding α-homoallylic alcohols has been developed using 20mol% [bmim][HSO4] as a metal activator, as well as a mediator for regioconversion from the initially formed γ-regiomer. The present protocol minimizes the use of conventional solvents and proceeds with good yields and excellent regioselectivities.

Catalytic Allylation of Aldehydes Using Unactivated Alkenes

Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.

Nickel-Catalyzed Homo- And Cross-Coupling of Allyl Alcohols via Allyl Boronates

A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B2pin2 with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling of the resulting allyl boronates with allyl alcohols. The method was effectively applied to nickel-catalyzed allylation of aldehydes using allylic alcohols directly.

Nickel-Catalysed Allylboration of Aldehydes

A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.

Synthesis of 1,3-disubstituted cyclohexenes from dienylethers: Via sequential hydrozirconation/deoxygenative cyclisation

Access to 1,3-disubstituted cyclohexenes from zirconocenes containing a latent electrophilic allylic fragment is described. Requiring a specific conformation, 6-endo-trig cyclisation is based on the TMSOTf-mediated generation of a stabilized carbocation.