5723-89-7

Upstream product

• 100-52-7 benzaldehyde 
• 110-83-8 cyclohexene 
• 1521-51-3 rac-3-bromocyclohexene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1165952-91-9 cyclohexa-1,3-diene 
• 17314-43-1 cyclohex-2-enyltrimethylstannane 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 112520-99-7 tributyl(cyclohex-2-en-1-yl)stannane 
• 536-74-3 phenylacetylene 
• 3420-52-8 1,4-Diphenylprop-3-en-1-one 
• 822-67-3 Cyclohex-2-enol 
• 18139-74-7 (+/-)-3-trichlorosilylcyclohexene 
• 3352-93-0 (S)-2-cyclohexenyl benzoate 
• 622-29-7 N-Benzylidenemethylamine 

Downstream Products

• 29373-01-1 cyclohex-2-en-1-yl(phenyl)methanone 
• 5723-84-2 (1-cyclohexen-3-yl)diphenylmethanol 
• 1616603-30-5 cyclohex-2-en-1-yl(phenyl)methanone acetyloxime 
• 1403477-88-2 (Z)-cyclohex-2-en-1-yl(phenyl)methanone oxime 
• 1403477-87-1 (E)-cyclohex-2-en-1-yl(phenyl)methanone oxime 

Relevant academic research and scientific papers

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.

Easy access to secondary and tertiary alcoholsviametal-free and light mediated radical carbonyl allylation

Here we report a strategy for carbonyl addition with unactivated alkenes using an organic photocatalyst on both aldehyde and ketone substrates. This protocol grants us a good alternative to the traditional Barbier-Grignard allylation that exhibits poor functional group tolerance. With this method the stoichiometric use of metals can be avoided, high atom economy can be achieved and fewer by-products are generated.

An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.

Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant CC Bond Cleavage

A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant CC bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.

Bismuth-Mediated Diastereoselective Allylation Reaction of Carbonyl Compounds with Cyclic Allylic Halides or Cinnamyl Halide

An efficient diastereoselective allylation of various carbonyl compounds with cyclic allylic halides by using commercially available bismuth powder in the presence of LiI was developed. Among all the metals screened, bismuth was found to be the best mediator for the transformation. The reactions involving various cyclic allylic halides proceeded smoothly at room temperature to produce the desired homoallylic alcohols in good to excellent yields with high diastereoselectivities (>99:1 dr). Reversed diastereoselectivity was obtained when carbonyl substrate (e. g., 2-pyridinecarboxaldehyde, glyoxylic acid) containing chelating substituent was used in the allylation reaction. In addition, the reactions involving acyclic (E)-cinnamyl bromide as substrate worked equally well with high diastereocontrol. (Figure presented.).

Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

Lead was found to efficiently mediate the allylation reactions of carbonyl compounds with cyclic allylic halides in the presence of stoichiometric amounts of lithium chloride and a catalytic amount of GaCl3 (20 mol %), leading to the desired homoallylic alcohols in modest to high yields with excellent diastereocontrol (>99:1 syn/anti) and good functional group tolerance. In contrast, the use of either 2-pyridinecarboxaldehyde as the carbonyl substrate or (E)-cinnamyl bromide as the allylating agent produced the corresponding product with reversed diastereoselectivity (>99:1 anti/syn).

Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)-H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis

We describe a hybrid system that realizes cooperativity between an organophotoredox acridinium catalyst and a chiral chromium complex catalyst, thereby enabling unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for asymmetric allylation of aldehydes. The reaction proceeds under visible light irradiation at room temperature, affording the corresponding homoallylic alcohols with a diastereomeric ratio >20/1 and up to 99% ee. The addition of Mg(ClO4)2 markedly enhanced both the reactivity and enantioselectivity.

Application of novel cross coupling reaction in preparing diastereotopic allyl alcohol compound

The invention relates to application of novel cross coupling reaction in preparing a diastereotopic allyl alcohol compound, and mainly provides a corresponding diastereotopic homoallyl alcohol compound obtained through high diastereoselective allylation r

Photocatalytic Barbier reaction-visible-light induced allylation and benzylation of aldehydes and ketones

We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols. The reaction proceeds at room temperature under visible light irradiation with the organic dye 3,7-di(4-biphenyl)1-naphthalene-10-phenoxazine as a photocatalyst and DIPEA as sacrificial electron donor. The proposed cross-coupling mechanism of a ketyl- and an allyl or benzyl radical is supported by spectroscopic investigations and cyclic voltammetry measurements.

Green Organocatalytic Dihydroxylation of Alkenes

An inexpensive, green, metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2-trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.