66205-43-4

Upstream product

• 24850-33-7 allyltributylstanane 
• 4553-07-5 ethyl phenylcyanoacetate 
• 108-86-1 bromobenzene 
• 106-95-6 allyl bromide 
• 105-56-6 ethyl 2-cyanoacetate 
• 3509-01-1 2-cyano-pent-4-enoic acid ethyl ester 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 1173722-19-4 C₁₂H₁₁NO₂ 
• 5558-87-2 2-phenylpent-4-enenitrile 

Relevant academic research and scientific papers

Nucleophile generation via decarboxylation: Asymmetric construction of contiguous trisubstituted and quaternary stereocenters through a Cu(I)-catalyzed decarboxylative mannich-type reaction

(Chemical Equation Presented) The first catalytic asymmetric decarboxylative Mannich-type reaction between aldimines and cyanocarboxylic acids was developed. α,α,β-Trisubstituted β-amino nitriles containing contiguous trisubstituted and all-carbon quatern

Tert-Butoxide-Mediated Arylation of 2-Substituted Cyanoacetates with Diaryliodonium Salts

A transition metal-free direct arylation of 2-substituted cyanoacetates with diaryliodonium salts was developed. With this approach, a wide range of α-tolunitrile derivatives has been synthesized in good to excellent yields of 45-92%. Furthermore, the practicability of this approach is further manifested in the synthesis of a related bioactive agent of glutarimide.

Cu(I)-catalyzed decarboxylative aldol-type and Mannich-type reactions for asymmetric construction of contiguous trisubstituted and quaternary stereocenters

The catalytic asymmetric decarboxylative aldol-type reaction between aldehydes and cyanocarboxylic acids and Mannich-type reaction between aldimines and cyanocarboxylic acids were developed. α,α,β-Trisubstituted- β-hydroxy nitriles bearing contiguous all-carbon quaternary and trisubstituted stereocenters were produced with moderate enantio- and diastereoselectivity in the presence of 10 mol % CuOAc-TANIAPHOS (or DTBM-SEGPHOS) complex in the aldol-type reaction. α,α,β- Trisubstituted-β-amino nitriles containing contiguous all-carbon quaternary and trisubstituted stereocenters were produced with moderate to high enantio- and diastereoselectivity using 5 mol % CuOAc-(R)-DTBM-SEGPHOS complex in the Mannich-type reaction. These reactions proceed through Cu(I)-catalyzed decarboxylative nucleophile generation, followed by the addition of the resulting chiral Cu-ketenimide to aldehydes or imines. Because the reactions proceed under very mild conditions at nearly neutral pH, the reactions are applicable to a wide range of substrate combinations, including both aromatic and aliphatic substrates. Finally, α,α,β-trisubstituted-β- amino nitriles were converted to β2,2,3-amino acid derivatives through simple acidic hydrolysis without any racemization and epimerization.

Palladium-catalyzed one-pot synthesis of 2-alkyl-2-arylcyanoacetates

(Chemical Equation Presented) A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a Pd(OAc)2/DPPF (DPPF = 1,1′-diphenylphosphino ferreocene)-catalyzed enolate arylation followed by in situ alkylation has been developed. This procedure tolerates a diverse range of aryl and heteroaryl bromides, and provides a rapid entry to a variety of 2-alkyl-2-arylcyanoacetates in good to excellent yield.

Palladium Catalysed Direct Allylation of Pronucleophiles with Allylstannanes

The reaction of pronucleophiles 1 with allyltributylstannanes in the presence of catalytic amounts of Pd2(dba)3*CHCl3 (4 molpercent) and 1,2-bis(diphenylphosphino)ethane (dppe) (10 molpercent) at room temperature gives the corresponding allylation products in good to high yields.