2082-61-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 2531, 1980 DOI: 10.1016/0040-4039(80)80120-1

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

Upstream product

• 4894-61-5 trans-but-2-enyl chloride 
• 2173-69-5 2-methyl-2-phenyl-propan-1-ol 
• 1565-75-9 2-phenyl-2-butanol 
• 515-40-2 neophyl chloride 
• 10467-10-4 ethylmagnesium iodide 
• 98-86-2 acetophenone 
• 925-90-6 ethylmagnesium bromide 
• 51380-79-1 β-phenylisovaleryl p-nitrobenzoyl peroxide 
• 62726-47-0 β-phenylisovaleryl peroxide 
• 87931-48-4 3-phenyl-pent-3-enoic acid 
• 4091-39-8 3-chloro-2-butanone 
• 591-51-5 phenyllithium 
• 100-42-5 styrene 
• 74-85-1 ethene 

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 
• 769-59-5 3-phenyl-butan-2-one 
• 33104-42-6 2,4-Diphenyl-3,4-dimethyl-hexen-⁽²⁾ 

Relevant academic research and scientific papers

NOBIN-based phosphoramidite and phosphorodiamidite ligands and their use in asymmetric nickel-catalysed hydrovinylation

Phosphoramidite and P-stereogenic phosphorodiamidite ligands derived from (Sa)-2-phenylamino-2′-hydroxy-1,1′-binaphthyl (N-Ph-NOBIN) and bis(1-phenyl-ethyl)amine were synthesised, fully characterised, and the absolute configuration of the stereogenic phosphorus atoms was assigned. The phosphoramidite ligand L2 features three non-bridged substituents at phosphorus comprising the bis(1-phenylethyl)amine and two NOBIN moieties. The NOBIN units are bound to the phosphorus through the oxygen atoms with two pendant nitrogen atoms. In the Ni-catalysed hydrovinylation of styrene no conversion was observed with the phosphorodiamidites, while the phosphoramidite ligands led to active catalysts with a marked co-operative effect on selectivities. Whereas the racemic product was obtained with the (S a,Sa,SC,SC) diastereomer, the (Sa,Sa,RC,RC) diastereomer proved to be one of the best ligands for this reaction, leading to almost perfect selectivity and ees of up to 91%.

Palladium-catalyzed asymmetric hydrovinylation under mild conditions using monodentate chiral spiro phosphoramidite and phosphite ligands

Palladium complexes of chiral spiro phosphoramidite and phosphite ligands are effective catalysts in the asymmetric hydrovinylation of vinylarenes with ethylene. The hydrovinylation products were obtained in modest selectivity with enantioselectivities up to 92% ee. The structures of the palladium catalysts have been analyzed by X-ray diffraction. The active catalyst contained one monodentate ligand. A kinetic resolution accompanied the isomerization of the hydrovinylation product in the reaction.

Highly selective cobalt-catalyzed hydrovinylation of styrene

Phosphine complexes of cobalt halide salts activated by diethylaluminum chloride are shown to yield highly active catalysts in the hydrovinylation of styrene, with unprecedented high selectivity to the desired product 3-phenyl-1-butene (3P1B). Double-bond isomerization, a common problem in codimerization reactions, only occurs after full conversion with these catalyst systems, even at elevated temperature. The most active catalysts are based on cobalt halide species combined with either C1- or C 2-bridged diphosphines, heterodonor P,N or P,O ligands, flexible bidentate phosphine ligands or monodentate phosphine ligands. Kinetic investigations show an order >1 in catalyst, which indicates either the involvement of dinuclear species in the catalytic cycle or partial catalyst decomposition via a bimolecular pathway.

Highly enantioselective nickel-catalyzed hydrovinylation with chiral phosphoramidite ligands

Readily available chiral phosphoramidites are a promising class of ligands for nickel-catalyzed asymmetric hydrovinylation of vinyl arenes. Cooperative effects are operative when ligands with more than one element of chirality are used. Choosing the prope

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.

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.

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.