767-99-7

Usage

Uses

Used in Chemical Synthesis:
trans-2-Phenyl-2-butene is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, making it a versatile building block in organic chemistry.
Used in Asymmetric Hydrogenation Studies:
In the field of catalysis, trans-2-Phenyl-2-butene is used as a reactant to study asymmetric hydrogenations. This application is particularly relevant for understanding the behavior of minimally functionalized olefins when catalyzed by iridium-containing complexes, which can lead to advancements in enantioselective synthesis and the development of more efficient catalysts.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its potential as a synthetic intermediate, trans-2-Phenyl-2-butene could also be used in the pharmaceutical industry for the synthesis of various drug molecules. Its ability to be modified and incorporated into more complex structures makes it a candidate for the development of new pharmaceutical agents.
Used in Materials Science:
Similarly, trans-2-Phenyl-2-butene could be utilized in materials science for the development of new polymers or materials with specific properties. Its structural characteristics may contribute to the creation of materials with tailored characteristics for various applications, such as in electronics, coatings, or adhesives.

InChI:InChI=1/C10H12/c1-3-9(2)10-7-5-4-6-8-10/h3-8H,1-2H3/b9-3-

Upstream product

• 135-98-8 sec-Butylbenzene 
• 925-90-6 ethylmagnesium bromide 
• 98-86-2 acetophenone 
• 51380-79-1 β-phenylisovaleryl p-nitrobenzoyl peroxide 
• 4091-39-8 3-chloro-2-butanone 
• 591-51-5 phenyllithium 
• 17988-58-8 12-<(phenylthio)ethyl>trimethylsilane 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 100-42-5 styrene 
• 74-85-1 ethene 
• 7719-09-7 thionyl chloride 
• 2173-69-5 2-methyl-2-phenyl-propan-1-ol 
• 826-54-0 2-methyl-2-phenyl-propanamide 
• 1565-75-9 2-phenyl-2-butanol 

Downstream Products

• 4564-81-2 1-phenyl-1,2-dimethyloxirane 
• 59341-61-6 3-phenylselenophene 
• 824-90-8 1-phenylbut-1-ene 
• 104-51-8 1-butylbenzene 
• 135-98-8 sec-Butylbenzene 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 143097-80-7 2-bromo-4-phenylbutane 
• 52392-57-1 2-bromo-3-phenyl-but-2c-ene 
• 52392-58-2 2-bromo-3-phenyl-but-2t-ene 
• 2404-87-7 3-phenylthiophene 
• 860687-81-6 (1,2-dibromo-1-methyl-propyl)-benzene 
• 65674-14-8 1,2-dibromo-4-phenylbutane 
• 52427-18-6 (+/-)-4-Hydroxy-1-(1-methyl-1-phenyl-propyl)-benzol 
• 40527-60-4 3-Brom-2-methyl-1,1,1-trinitro-2-phenyl-butan 

Relevant academic research and scientific papers

Modular Ni(0)/Silane Catalytic System for the Isomerization of Alkenes

Alkenes are used ubiquitously as starting materials and synthetic targets in all areas of chemistry. Controlling their geometry and position along a chain is vital to their reactivity and properties yet remains challenging. Alkene isomerization is an atom-economical process to synthesize targeted alkenes, and selectivity can be controlled using transition metal catalysts. The development of mild, selective isomerization reactivity has enabled efficient tandem catalytic systems for the remote functionalization of alkenes, a process in which a starting alkene is isomerized to a new position prior to the functionalization step. The key challenges in developing isomerization catalysts for remote functionalization applications are (i) a lack of modularity in the catalyst structure and (ii) the requirement of nonmodular and/or harsh additives during catalyst activation. We address both challenges with a modular (NHC)Ni(0)/silane catalytic system (NHC, N-heterocyclic carbene), demonstrating the use of triaryl silanes and readily accessible (NHC)Ni(0) complexes to form the proposed active (NHC)(silyl)Ni-H species in situ. We show that modification of the steric and electronic nature of the catalyst via modification of the ancillary ligand and silane partner, respectively, is easily achieved, creating a uniquely versatile catalytic system that is effective for the formation of internal alkenes with high yield and selectivity for the E-alkene. The use of silanes as mild activators enables isomerization of substrates with a variety of functional groups, including acid-labile groups. The broad substrate scope, enabled by catalyst design, makes this catalytic system a strong candidate for use in tandem catalytic applications. Preliminary mechanistic studies support a Ni-H insertion/elimination pathway.

Regioselective Three-Component Synthesis of Vicinal Diamines via 1,2-Diamination of Styrenes

The vicinal diamine motif plays a significant role in natural products, drug design, and organic synthesis, and development of synthetic methods for the synthesis of diamines is a long-standing interest. Herein, we report a regioselective intermolecular three-component vicinal diamination of styrenes with acetonitrile and azodicarboxylates. The diamination products can be produced in moderate to excellent yields via the Ritter reaction. Synthetic applications and theoretical studies of this reaction have been conducted.

Mono-Gold(I)-Catalyzed Enantioselective Intermolecular Reaction of Ynones with Styrenes: Tandem Diels–Alder and Ene Sequence

Gold-catalyzed intermolecular reaction leading to dihydronaphthalene derivatives in one pot from two equivalents of ynones with respect to styrene is uncovered. The [4+2] Diels–Alder cycloaddition of ynones and styrenes is catalyzed by a mono-gold(I) complex and the conjugated acid to provide an unstable 3,8a-dihydronaphthalene to subsequently undergo an intermolecular ene-type reaction with the π-activated ynone to afford multi-component coupling dihydronaphthalene products. Linear relationships between chiral ligand-gold complexes and chiral dihydronaphthalene products proves mono-gold catalysis that triggers an asymmetric tandem Diels–Alder and ene reaction sequence.

Visible-Light-Induced Meerwein Fluoroarylation of Styrenes

An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Highly Stereoselective Positional Isomerization of Styrenes via Acid-Catalyzed Carbocation Mechanism

The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Br?nsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this protocol is further highlighted by the gram-scale synthesis, high stereoselectivity, good functional group tolerance, and simple operation. Mechanistic studies support that Al(OTf)3 acts as a hidden Br?nsted acid catalyst and a carbocation intermediate is formed.

The effects of using an ionic liquid as a solvent for a reaction that proceeds through a phenonium ion

A unimolecular reaction that proceeds predominantly through a phenonium ion intermediate was investigated in mixtures of an ionic liquid and methanol. Varying the proportion of the ionic liquid in the reaction mixture led to an increase in the rate constant compared with methanol when very small amounts of ionic liquid were present in the reaction mixture and a decrease when higher proportions of the salt were present. Activation parameters determined for the process showed that the effect of changing the solvent composition on the rate constant was due to a key interaction between the ionic liquid and the transition state of the process, similar to other unimolecular processes. Analysis of the stereochemistry of the products demonstrated that the ionic liquid had no effect on either the ratio of the stereochemistry of the substitution products, or the ratio of the substitution and eliminations mechanisms occurring in solution.

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

Aqueous ZnCl2 Complex Catalyzed Prins Reaction of Silyl Glyoxylates: Access to Functionalized Tertiary α-Silyl Alcohols

An efficient Prins reaction of silyl glyoxylates in the presence of an aqueous ZnCl2 complex as a catalyst was developed, providing functionalized tertiary α-silyl alcohols in high yields under mild conditions. A preliminary investigation indicated that the aqueous ZnCl2 complex acted as a dual functional catalyst of Br?nsted and Lewis acid to activate the carbonyl groups of silyl glyoxylates via a dual-activation model.

Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes

Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.