54976-37-3

Upstream product

• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 1196-67-4 3-phenyl-2-butenal 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 7664-93-9 sulfuric acid 
• 50-00-0 formaldehyd 
• 98-83-9 isopropenylbenzene 
• 704-79-0 3-phenylbut-2-enoic acid 
• 1794-51-0 1-chloro-3-phenyl-2-butene 
• 264910-19-2 2-methoxy-2-phenyl-3-butene 
• 108-86-1 bromobenzene 
• 504-61-0 (E)-but-2-enol 
• 1196-67-4 (Z)-3-Phenyl-but-2-en-1-al 
• 1504-72-9 ethyl 3-phenylbut-2-enoate 
• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 

Downstream Products

• 39171-59-0 (4-bromobut-2-en-2-yl)benzene 
• 107475-99-0 ethyl-(3-phenyl-but-2-enyl)-ether 
• 171083-61-7 4-methyl-4-phenylhex-5-en-2-one 
• 36920-29-3 4-methyl-4-phenylcyclopent-2-en-1-one 
• 144632-53-1 2-methyl-4-oxo-2-phenylpentanal 
• 273377-11-0 (E)-3-phenylbut-2-enyl 2,2,2-trichloroethanimidoate 
• 2031-46-1 (R)-3-phenylbutanol 
• 2031-46-1 (3S)-3-phenylbutan-1-ol 
• 1332645-38-1 (R)-4-phenyl-6-(trifluoromethyl)-6-(4-chlorophenyl)-5,6-dihydro-2H-pyran-2-one 
• 1332645-27-8 (R)-4-phenyl-6-(trifluoromethyl)-6-phenyl-5,6-dihydro-2H-pyran-2-one 
• 1377848-07-1 (R)-4-phenyl-6-p-tolyl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one 
• 1377848-08-2 (R)-6-(4-bromophenyl)-4-phenyl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one 
• 1377848-09-3 (S)-4-phenyl-6-(thiophen-2-yl)-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one 
• 1377848-11-7 (S)-6-methyl-4-phenyl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono- and Dibromospiroketals

Employing halenium affinity (HalA) as a guiding tool, the weak nucleophilic character of alkyl ketones was modulated by the templating effect of a tethered 2-tetrahydropyranyl(THP)-protected alcohol towards realizing a bromenium ion initiated spiroketaliz

Complementary Photocatalytic Toolbox: Control of Intramolecular endo-versus exo-trig Cyclizations of α-Phenyl Olefins to Oxaheterocyclic Products

The regioselectivity of the intramolecular cyclization of bifunctional α-phenyl alkenes can be controlled simply by the choice of the organic chromophore as the photocatalyst. The central photoredox catalytic reaction in both cases is a nucleophilic addition of the hydroxyl function to the olefin function of the substrates. N,N-(4-Diisobutylaminophenyl) phenothiazine catalyzes exo-trig cyclizations, whereas 1,7-dicyanoperylene-3,4,9,10-tetracarboxylic acid bisimides catalyze endo-trig additions to products with anti-Markovnikov regioselectivity. We preliminarily report the photoredox catalytic conversions of 11 representative substrates into 20 oxaheterocycles in order to demonstrate the similarity, but also the complementarity, of these two variants in this photoredox catalytic toolbox.

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences

Energy-transfer processes involving copper complexes are rare. Using an optimized heteroleptic copper complex, Cu(bphen)(XantPhos)BF4, photosensitized E → Z isomerization of olefins is demonstrated. The XantPhos ligand afforded sensitizers with improved catalyst stability, while the bphen ligand lengthened the excited-state lifetime. A series of 25 di- and trisubstituted alkenes underwent photoisomerization, including macrocycles and 1,3-enynes. Cu(bphen)(XantPhos)BF4 could also be employed in a tandem ATRA/photoisomerization process employing arylsulfonyl chlorides, an example of photoisomerization with halide-substituted olefins.

Strong acid-catalyzed electrophilic ring expansion of oxetanes and sulfoxonium ylides

A strong protic acid-catalyzed electrophilic ring expansion of oxetanes into trans-2,3-disubstituted tetrahydrofuran derivatives using sulfoxonium ylides has been developed. This reaction produces functionalized trans-2,3-disubstituted tetrahydrofuran derivatives stereospecifically by using safe and stable sulfoxonium ylides without metal catalysts and the protection of inert gas.

Selective Synthesis of Z-Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light-Promoted Photocatalytic E to Z Isomerization

A photocatalytic E to Z isomerization of alkenes using an iridium photosensitizer under mild reaction conditions is disclosed. This method provides scalable and efficient access to Z-cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity. Importantly, this method also provides a powerful strategy for the selective synthesis of Z-magnolol and honokiol derivatives possessing potential biological activity.

Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles

A carbene-catalyzed oxidative cycloaddition reaction is developed for efficient access to multi-functionalized 2-phenylbenzothiazoles. A broad scope of heavily substituted arenes bearing 2-benzothiazole groups have been prepared in good to excellent yields. The remote C(sp2)–H bond in the substituted arene products can be activated by Pd catalysts in regio-selective fashion with the direction of the 2-benzothiazole groups.

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.

Catalytic Regioselective Isomerization of 2,2-Disubstituted Oxetanes to Homoallylic Alcohols

The selective isomerization of strained heterocyclic compounds is an important tool in organic synthesis. An unprecedented regioselective isomerization of 2,2-disubstituted oxetanes into homoallylic alcohols is described. The use of tris(pentafluorophenyl

Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade

A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.