54976-39-5

Upstream product

• 54976-37-3 (Z)-3-phenyl-2-buten-1-ol 
• 3461-50-5 methyl (Z)-3-phenyl-but-2-enoate 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 945-93-7 ethyl (Z)-3-phenylbut-2-enoate 
• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 98-86-2 acetophenone 
• 3461-50-5 methyl trans-3-methylcinnamate 
• 108-86-1 bromobenzene 
• 1504-72-9 ethyl 3-phenylbut-2-enoate 
• 54976-37-3 3-phenylbut-2-en-1-ol 
• 2293-60-9 ethyl 3-hydroxy-3-phenylbutyrate 

Downstream Products

• 1182847-30-8 (S)-(3-methylhept-1-en-3-yl)benzene 
• 53109-17-4 2-phenyl-2-(Z)-octene 
• 1374760-62-9 (-)-(R)-(3-methylhept-1-en-3-yl)benzene 
• 20826-50-0 (Z)-hex-2-en-2-ylbenzene 
• 768392-48-9 (R)-(-)-3-methyl-3-phenyl-1-pentene 
• 137595-11-0 (Z)-2-phenyl-2-decene 
• 38607-88-4 C₄₀H₄₄ 
• 1047082-67-6 C₁₇H₁₆O₂ 
• 1159583-01-3 C₁₈H₁₈O 
• 1234462-68-0 (E)-p-methoxycinnamyl (E)-3-methylcinnamyl ether 
• 1583276-66-7 (E)-2,2-dimethyl-1,5-diphenylhex-4-en-1-one 
• 1583276-53-2 (1Z,4E)-2,2-dimethyl-1,5-diphenylhex-4-en-1-one oxime 
• 1583276-32-7 4,4-dimethyl-5-phenyl-2-(1-phenylethyl)-3,4-dihydro-2H-pyrrole 1-oxide 

Relevant academic research and scientific papers

Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant

Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.

Inter-and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes

Inter-and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl 4or SnBr 4stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides, including in situ generated derivatives, showed high diversity of reaction modes depending on the structures and substituents of the substrates. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were discussed based on the DFT calculations.

Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors

We report herein an unprecedented protocol for radical cyclization of aldehydes with pendant alkenes via synergistic photoredox, cobaloxime, and amine catalysis. The transformation was achieved in the absence of external oxidants, providing a variety of 5-, 6-, and 7-membered ring products with alkene transposition in satisfactory yields. The reaction exhibits wide functional group compatibility and occurs under mild conditions with extrusion of H2.

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.

Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

SmI 2 -catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter

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.

P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation

Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes

The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary result, asymmetric formylation was conducted using a menthol-derived chiral thioformate.

Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective hydride transfer to allylic bromides, an allylic reduction. The resulting aryl- and alkyl-substituted branched α-olefins, which are valuable building blocks for synthesis, are obtained in good yields and regioselectivity. A commercially available silane, (TMSO)2Si(Me)H, is employed as hydride source. This protocol offers a unified alternative to the established metal-catalyzed allylic substitutions with carbon nucleophiles, as no adaption of the catalyst to the nature of the nucleophile is required.

Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives

Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4?+?2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.