1416985-75-5

Basic information

• Product Name: 2,2,2-trifluoro-N-(5'-((triethylsilyl)oxy)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-4-yl)acetamide
• Synonyms: 2,2,2-trifluoro-N-(5'-((triethylsilyl)oxy)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-4-yl)acetamide
• CAS NO: 1416985-75-5
• Molecular Weight: 399.529
• Mol File: 1416985-75-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,2,2-trifluoro-N-(5'-((triethylsilyl)oxy)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-4-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-trifluoro-N-(5'-((triethylsilyl)oxy)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-4-yl)acetamide(1416985-75-5)
• EPA Substance Registry System: 2,2,2-trifluoro-N-(5'-((triethylsilyl)oxy)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-4-yl)acetamide(1416985-75-5)

Safety Data

• Hazardous Substances Data: 1416985-75-5(Hazardous Substances Data)

Upstream product

• 930-68-7 cyclohexenone 
• 994-30-9 triethylsilyl chloride 
• 126063-08-9 2,2,2-trifluoro-N-(4-iodophenyl)acetamide 

Relevant articles and documents

Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates

An alternative method to copper-catalyzed conjugate addition followed by enolate silylation for the synthesis of β-disubstituted silyl enol ether products (R1(R2)HCCH=C(OSiR43)R 3) is presented. This method uses haloarenes instead of nucleophilic aryl reagents. Nickel ligated to either neocuproine or bipyridine couples an α,β-unsaturated ketone or aldehyde (R2HC=CHC(O)R 3) with an organic halide (R1-X) in the presence of a trialkylchlorosilane reagent (Cl-SiR43). Reactions are assembled on the benchtop and tolerate a variety of functional groups (aldehyde, ketone, nitrile, sulfone, pentafluorosulfur, and N-aryltrifluoroacetamide), electron-rich iodoarenes, and electron-poor haloarenes. Mechanistic studies have confirmed the first example of a catalytic reductive conjugate addition of organic halides that proceeds via an allylnickel intermediate. Selectivity is attributed to (1) rapid, selective reaction of LNi0 with chlorotriethylsilane and enone in the presence of other organic electrophiles, and (2) minimization of enone dimerization by ligand steric effects.