33326-56-6

Upstream product

• 300-57-2 allylbenzene 
• 100-44-7 benzyl chloride 
• 821-06-7 (E)-1,4-dibromobutene 
• 74-85-1 ethene 
• 38111-44-3 phenylzinc(II) bromide 
• 1589-82-8 phenylmagnesium bromide 
• 104-54-1 3-Phenylpropenol 
• 591-50-4 iodobenzene 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 768-56-9 4-Phenylbut-1-ene 
• 100-58-3 phenylmagnesium bromide 
• 5281-18-5 benzaldehyde, hydrazone 
• 7217-71-2 1-phenyl-2-propenyl acetate 

Downstream Products

• 35030-49-0 Methyl 2,3-diphenylpropanoate 

Relevant academic research and scientific papers

Copper and palladium co-catalyzed highly regio-selective 1,2-hydroarylation of terminal 1,3-dienes

A practical copper and palladium co-catalyzed highly regio-selective hydroarylation of terminal 1,3-dienes has been developed. This chemistry afforded the terminal alkenyl group containing products, which are a kind of versatile precursor for organic synthesis, from 1,3-dienes by a practical one-step reaction. With good functional group tolerance, this protocol could be used to make a series of bio-active compounds using readily accessible starting materials. The mechanism of this reaction was explored by control experiments and kinetics studies. This journal is

Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes

The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Chemo- and regioselective C(sp3)-H arylation of unactivated allylarenes by deprotonative cross-coupling

The combination of aryl bromides, allylbenzene, base and a palladium catalyst usually results in a Heck reaction. Herein we combine these same reagents, but override the Heck pathway by employing a strong base. In the presence of LiN(SiMe3)sub

Clear-cut difference in the rearrangement of 1-bromo-2-(2-phenyl-3-butenyl) benzene under anionic or radical conditions

The o-(3-butenyl)phenyl system bearing a phenyl group on the 2-position of the side chain was studied as a potential mechanistic probe for distinguishing between radical and carbanion intermediates. The Bu3SnH reduction of 1-bromo-2-(2-phenyl-3

Cu(I)-catalyzed, α-selective, allylic alkylation reactions between phosphorothioate esters and organomagnesium reagents

Regiocontrol of allylic alkylation reactions involving hard nucleophiles remains a significant challenge and continues to be an active area of research. The lack of general methods in which α-alkylation is favored underscores the need for the development of new processes for achieving this type of selectivity. We report that Cu(I) catalyzes the allylic substitution of phosphorothioate esters with excellent α-regioselectivity, regardless of the nature of the Grignard reagent that is used. To the best of our knowledge, the Cu-catalyzed allylic alkylation of phosphorothioate esters has never been described. We have also developed a simple protocol for inducing high α selectivity starting from secondary allylic halides. This is accomplished by using sodium phosphorothioates as an additive.

Copper-catalyzed asymmetric allylic substitution with aryl and ethyl Grignard reagents

Phenyl- and ethyl-magnesium bromides undergo regioselective asymmetric allylic substitution with high enantioselectivity under the catalysis of chiral amidophosphane-copper(i) complexes. The Royal Society of Chemistry.

Decarboxylative allylation using sulfones as surrogates of alkanes

(Chemical Equation Presented) α-Sulfonyl functional groups are traceless activating groups that facilitate catalytic decarboxylative allylations in high yield yet can be cleaved to allow the synthesis of simple allylated alkanes. Substrate studies suggest

Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: Inversion of absolute configuration

The transition metal-catalyzed allylic substitution with unstabilized carbon nucleophiles represents an important cross-coupling reaction for the construction of ternary carbon stereogenic centers. We have developed a new regio- and enantiospecific rhodium-catalyzed allylic alkylation of acyclic unsymmetrical chiral nonracemic allylic alcohol derivatives with aryl zinc bromides. This study demonstrates that the hydrotris(pyrazolyl)borate rhodium catalyst and zinc(II) halide salt are crucial for efficiency, while the addition of lithium bromide to the catalyst is necessary for obtaining optimal regiospecificity. The stereochemical course of this reaction was established through the synthesis of (S)-ibuprofen, which demonstrated that the alkylation proceeds with net inversion of absolute configuration consistent with direct addition of the nucleophile to the metal center followed by reductive elimination. Copyright

Titanocene(II)-promoted reactions of thioacetals with ethylene: Selective formation of terminal olefins with one- or two-carbon homologation

Thioacetals are selectively transformed into two types of terminal olefins, one with one-carbon homologation and the other with two-carbon homologation, by treatment with a titanocene(II) species under ethylene. The mode of the reaction is controlled by changing the ligands coordinated to titanocene(II).