102614-91-5

Upstream product

• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 3282-30-2 pivaloyl chloride 
• 1896-62-4 (E)-benzalacetone 

Downstream Products

• 1529809-38-8 C₁₇H₁₈O 
• 1613507-14-4 (S,E)-methyl(4-(4-phenylbut-3-en-2-yl)phenyl)sulfane 
• 1613507-15-5 (S,E)-1-(4-phenylbut-3-en-2-yl)-4-vinylbenzene 
• 1613507-17-7 (S,E)-1-bromo-4-(4-phenylbut-3-en-2-yl)benzene 
• 1613507-18-8 (S,E)-1-(4-phenylbut-3-en-2-yl)-4-(trifluoromethyl)benzene 
• 1352656-46-2 (S, E)-methyl 4-(4-phenylbut-3-en-2-yl)benzoate 
• 1380310-87-1 (R, E)-methyl 4-(4-phenylbut-3-en-2-yl)benzoate 
• 1613507-19-9 (S,E)-1-(3-(4-phenylbut-3-en-2-yl)phenyl)ethanone 
• 1613507-20-2 (S,E)-3-(4-phenylbut-3-en-2-yl)benzonitrile 
• 1613507-21-3 (S,E)-5-(4-phenylbut-3-en-2-yl)benzo[d][1,3]dioxole 
• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 1391742-83-8 (R)-2-(4-phenylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 2344-70-9 (R)-4-phenyl-2-butanol 

Relevant academic research and scientific papers

Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.

Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates

We have developed a stereospecific, nickel-catalyzed Miyaura borylation of allylic pivalates, which delivers highly enantioenriched α-stereogenic γ-aryl allylboronates with good yields and regioselectivities. Our complementary sets of conditions enable access to either enantiomer of allylboronate product from a single enantiomer of readily prepared allylic pivalate substrate. Excellent functional group tolerance, yields, regioselectivities, and stereochemical fidelities are observed. The stereochemical switch from stereoretention to stereoinversion largely depends upon solvent and can be explained by competitive pathways for the oxidative addition step. Our mechanistic investigations support a stereoretentive pathway stemming from a directed oxidative addition and a stereoinvertive pathway that is dominant when MeCN blocks coordination of the directing group by binding the nickel catalyst.

Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines

We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.