575452-49-2

Upstream product

• 5470-84-8 4-benzyloxybutanal 
• 1730-25-2 allylmagnesium bromide 
• 591-87-7 Allyl acetate 
• 81518-74-3 1-benzyloxy-4-pentene 
• 100-39-0 benzyl bromide 
• 83458-88-2 (+/-)-5-benzyloxy-1,2-pentanediol 
• 762-72-1 allyl-trimethyl-silane 
• 17891-78-0 1,3-bis(trimethylsilyl)propene 
• 106-95-6 allyl bromide 
• 2622-05-1 allylmagnesium bromide 

Downstream Products

• 1061370-35-1 C₁₆H₂₂O₄ 
• 1315277-95-2 C₂₂H₂₈O₃ 
• 1234691-64-5 S-ethyl 6-benzyloxy-3-(4-methoxybenzyloxy)-1-hexanethioate 
• 1234691-65-6 S-(4-methylphenyl) 6-benzyloxy-3-(4-methoxybenzyloxy)-1-hexanethioate 
• 1234691-67-8 S-phenyl 6-benzyloxy-3-(4-methoxybenzyloxy)-1-hexanethioate 
• 1234691-68-9 S-(4-nitrophenyl) 6-benzyloxy-3-(4-methoxybenzyloxy)-1-hexanethioate 
• 1234691-45-2 1-benzyloxy-4,11-bis(4-methoxybenzyloxy)-7-undecyn-6-one 
• 1234691-48-5 1-benzyloxy-4-(4-methoxybenzyloxy)-7-dodecyn-6-one 
• 1309376-15-5 C₃₄H₄₂O₄Si 
• 1309376-17-7 C₂₁H₂₂O₃ 
• 1309376-18-8 C₂₁H₂₈O₃ 
• 1309376-96-2 C₂₆H₃₂O₄ 
• 1315277-89-4 (7E)-1-benzyloxy-4-hydroxy-7-undecen-6-one 
• 1315277-68-9 6-benzyloxy-3-(4-methoxybenzyloxy)-1-hexanal 

Relevant academic research and scientific papers

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex

The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2-phenylpyridine, 2 mol %), and N,N-diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. (Figure presented.).

Cp2TiCl2-Catalyzed Photoredox Allylation of Aldehydes with Visible Light

A Barbier-type Cp2TiCl2-mediated (10 mol %) photoredox allylation of aldehydes under irradiation with visible light (blue light-emitting diodes (LEDs), 450 nm) and in the presence of an organic dye (3DPAFIPN, 5 mol %) with allylbromides is described.

Allylation of aldehydes by dual photoredox and nickel catalysis

Here we report the application of dual nickel/photoredox catalysis to the allylation of aliphatic, aromatic and heteroaromatic aldehydes by using commercially available reagents. The process utilizes the combination of a Ni(ii) complex, [Ru(bpy)3]2+ as a photoredox catalyst, and allylacetate under blue LED irradiation, and allows the synthesis of a large variety of homoallylic alcohols.

Green organocatalytic synthesis of isoxazolines via a one-pot oxidation of allyloximes

A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in moderate to excellent yields.

A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters

In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an efficient manner under mild conditions. AgOTf-promoted intramolecular oxa-conjugate cyclization of β-hydroxy ynones provided 2,6-substituted dihydropyrones in excellent yields. On the other hand, acid-catalyzed cyclization of β-hydroxy enones caused racemization of the product 2,6-substituted tetrahydropyrones due to its reversible nature. Eventually, stereoselective hydrogenation of substituted dihydropyrones was found to be a solid and efficient approach for the synthesis of 2,6-cis-substituted tetrahydropyrone derivatives.

Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes

The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.

Stereoselective synthesis of versatile 2-chloromercurium-3,5-syn-dihydroxy esters via intramolecular oxymercuration

Regio- and stereocontrolled alkoxy mercuration of α,β-unsaturated esters allows direct access to 1,3-syn diols in good yields. Demercuration of adducts leads to 1,3 skipped dihydroxy esters, alcohols, and α-halo esters. The deprotection of acetonide with Amberlyst 15 on 1,3-syn-dihydroxy esters gives the corresponding δ-lactones.