399032-28-1

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 74-85-1 ethene 
• 1394035-47-2 (2E)-but-2-en-1-yl 4-(trifluoromethyl)phenyl ether 
• 5467-74-3 4-Bromophenylboronic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 96090-12-9 p-bromo-cinnamyl bromide 
• 917-54-4 methyllithium 

Downstream Products

• 36617-88-6 (R)-3-phenyl-1-butene 
• 58717-85-4 (S)-3-phenyl-1-butene 
• 114937-27-8 (2R)-2-<4-(2-Methylpropyl)phenyl>propanal 
• 51146-57-7 (R)-ibuprofene 

Relevant academic research and scientific papers

Low-Pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes

An efficient and practical protocol for the enantioselective cobalt-catalyzed hydrovinylation of vinylarenes with ethylene at low (1.2 bar) pressure has been developed. As precatalysts, stable [L2CoCl2] complexes are employed that are activated in situ with Et2AlCl. A modular chiral TADDOL-derived phosphine-phosphite ligand was identified that allows the conversion of a broad spectrum of substrates, including heterocyclic vinylarenes and vinylferrocene, to smoothly afford the branched products with up to 99 % ee and virtually complete regioselectivity. Even polar functional groups, such as OH, NH2, CN, and CO2R, are tolerated.

Room temperature highly enantioselective nickel-catalyzed hydrovinylation

At room temperature, nickel catalysts based on the new phosphoramidite (11bR)-N-[(S)-1-(naphthalen-1-yl)ethyl]-N-[(S)-1-(naphthalen-2-yl)ethyl] dinaphtho[2,1-d:1, 2'-f] [1,3,2]dioxaphosphepin-4-amine provide excellent selectivities for 3-arylbut-1-enes (9

Synthesis of optically active β- Or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents

An efficient one-pot synthesis of optically active β-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral γ-alkyl-substituted alcohols.

Rhodium-catalyzed asymmetric coupling reaction of allylic ethers with arylboronic acids

An asymmetric allylic substitution of simple allylic ethers with arylboronic acids in the presence of a rhodium(I)/(R)-DTBM-SEGPHOS catalyst has been developed. The reactions proceeded smoothly at room temperature to give the corresponding branch products with excellent regioselectivities and good to excellent enantioselectivities.

Enantioselective hydrovinylation via asymmetric counteranion-directed ruthenium catalysis

The first Ru-catalyzed enantioselective hydrovinylation has been realized by using an asymmetric counteranion-directed catalysis strategy. Styrene derivatives react with ethylene in excellent yields and promising enantioselectivity using this approach. Th

Tunable phosphinite, phosphite and phosphoramidite ligands for the asymmetric hydrovinylation reactions

Only a limited number of ligands have been successfully employed for the Ni-catalyzed asymmetric hydrovinylation reaction. Diarylphosphinites, carrying β-acylamino groups prepared from readily available carbohydrates, in conjunction with highly dissociated counteranions {[(3,5-(CF3) 2C6H3]4B- or SbF 6-}, effect the hydrovinylation of vinylarenes under ambient pressure of ethylene with high enantioselectivity. Nitrogen substituents such as -COCF3 and COPh groups lead to isomerization of the primary products (3-arylbutenes) to Z- and E-2-aryl-2-butenes. In a prototypical synthesis of a 2-arylproionic acid, (S)-3-(4-bromophenyl)-1-butene (89% ee) has be transformed into (R)-ibuprofen by Ni-catalyzed cross-coupling with i-BuMgBr, followed by oxidation of the double bond with NaIO4 and KMnO 4. Asymmetric codimerization of norbonene and ethylene using binaphthol-derived phosphoramidites as ligands gives 1:1, 2:1 or polymeric adducts depending on the relative configurations and nature of the BINAP and amine moieties. With one of the phosphoramidite-Ni complexes, counteranions BAr4- [Ar=3,5-(CF3)2C 6H3] and SbF6-, which had been used interchangeably in other reactions, give either a 1:1 adduct or a 2:1 adduct, respectively.

Fine-tuning monophosphine ligands for enhanced enantioselectivity. Influence of chiral hemilabile pendant groups

C2-Symmetric P-(2-X-aryl)-2,5-dialkylphospholanes (X = dioxolan-2-yl or dioxan-2-yl), designed on the basis of a working model for asymmetric induction, are effective ligands for the Ni(II)-catalyzed asymmetric hydrovinylation of styrenes. Excellent yields (>99%), selectivities for the desired 3-arylbutenes (>99%), high S/C ratios (>1200), and ee's (up to 91%) have been realized for a number of prototypical vinylarenes. In the dioxolane series, the selectivity depends on the configuration of the C 4 and C5 carbons.

Tunable ligands for asymmetric catalysis: Readily available carbohydrate-derived diarylphosphinites induce high selectivity in the hydrovinylation of styrene derivatives

Only a limited number of ligands have been successfully employed for the Ni-catalyzed asymmetric hydrovinylation reaction. Diarylphosphonites prepared from readily available carbohydrates in conjunction with a highly dissociated counterion ([3,5-(CF3

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