1142813-45-3

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 
• 947-77-3 1-methyl-2-(1-phenylvinyl)benzene 
• 100-42-5 styrene 
• 16419-60-6 2-Methylphenylboronic acid 

Relevant academic research and scientific papers

Chiral Iridium Complexes of Anionic NCP Pincer Ligand for Asymmetric Transfer Hydrogenation of 1,1-Diarylethenes with Ethanol

Chiral iridium complexes ligated by anionic oxazoline-bearing NCP-type pincer ligands were developed and applied to the asymmetric transfer hydrogenation (ATH) of diarylethenes using environmentally benign ethanol as the hydrogen donor. High enantioselectivities could be achieved for substrates bearing ortho-Me, ortho-Cl, or ortho-Br substituents on one of the aryl groups. The ATH of ortho-Br-substituted diarylethenes is particularly attractive due to the propensity of the C(aryl)-Br bond to undergo various new bond-forming events.

Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes

The enantioselective hydroarylation of vinylarenes catalyzed by a chiral, non-racemic nickel catalyst is presented as a facile method to generate chiral 1,1-diarylethanes. These reactions proceed via formation of a chiral, non-racemic nickel benzyl intermediate. Transmetalation with arylboron nucleophiles and subsequent reductive elimination enable the formation of a variety of chiral 1,1-diarylethanes. The 1,1-diarylethane products from reactions of arylboronic acids containing electron-donating substituents are formed with typically greater than 90% ee, while the 1,1-diarylethanes generated from reactions of arylboronic acids containing electron-withdrawing groups are generated with typically less than 80% ee. These results are consistent with the rate of transmetalation with an arylboron nucleophile playing a key role in the enantioselectivity of these hydroarylation reactions. This mechanistic insight has led to the development of reactions of neo-pentylglycolate esters of arylboronic acids with vinylarenes that occur with higher enantioselectivities based on increased rates of transmetalation.

Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes

We have developed a Ni-catalyzed enantioselective hydroarylation of styrenes with arylboronic acids using MeOH as the hydrogen source, providing an efficient method to access 1,1-diarylalkanes, which are essential structural units in many biologically active compounds. In addition, Ni-catalyzed enantioselective hydrovinylation of styrenes with vinylboronic acids is also realized with good yields and enantioselectivities. The synthetic utility was demonstrated by the efficient synthesis of (R)-(-)-ibuprofen.

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Highly chemoselective and enantiospecific Suzuki-Miyaura cross-couplings of benzylic organoboronic esters

The use of potassium carbonate in addition to silver oxide is shown to increase the enantiospecificity of the Suzuki-Miyaura cross-coupling reaction of chiral secondary benzylic boronic esters. From mechanistic studies, it is shown that the reaction is co

COBALT PHOSPHINE ALKYL COMPLEXES FOR THE ASYMMETRIC HYDROGENATION OF ALKENES

Disclosed herein are manganese, iron, nickel, or cobalt compounds having a bidentate ligand and the use of these compounds for the hydrogenation of alkenes, particularly the asymmetric hydrogenation of prochiral olefins.