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Chemical Structure| 16635-95-3 Chemical Structure| 16635-95-3

Structure of 16635-95-3

Chemical Structure| 16635-95-3

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Connor Q. Kabes ; Reagan F. Lucas ; Jack H. Gunn ; John A. Gladysz ;

Abstract: The lipophilic diastereomeric cobalt complexes Λ or Δ-[Co((S,S)-dpen)3]3+ 2Cl–BArf– (Λ or Δ-(S,S)-23+ 2Cl–BArf–; dpen/BArf– = 1,2-diphenylethylenediamine/B(3,5-C6H3(CF3)2)4–) catalyze a number of enantioselective C–H bond addition reactions in the presence of aliphatic tertiary amines, but pyridine and N,N-dimethylaniline are much less effective. However, when these bases are incorporated into counter anions (4–) as in Λ or Δ-(S,S)-23+4–Cl–BArf–, highly enantioselective bifunctional catalysts can be realized. Salts of nicotinates, isonicotinates, related sulfonates, and N,N-dimethylaminobenzoate are effective. The 6-chloronicotinate salt gives slower rates and lower ee values, and the 6-aminonicotinate salt gives faster rates and higher ee values. The 6-methyl, 2-methoxy, and unsubstituted analogs afford intermediate results. The 6-aminonicotinate catalyst is applied to additions of dimethyl malonate to 14 aryl-substituted nitroolefins and additions of 6 1,3-dicarbonyl compounds to di-t-butyl azodicarboxylate, with average yields/ee values of 90%/85% and 94%/77%, respectively. The authors are unaware of other ionic catalysts for which Brønsted bases have been productively incorporated into the anions, which are seldom if ever purposefully functionalized in any manner.

Keywords: cobalt ; 1,2-diamines ; smart anions ; task specific anions ; hydrogen bonding ; bifunctional catalysts ; enantioselective catalysis ; Michael additions

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Product Details of [ 16635-95-3 ]

CAS No. :16635-95-3
Formula : C14H16N2
M.W : 212.29
SMILES Code : N[C@H](C1=CC=CC=C1)[C@@H](C2=CC=CC=C2)N
MDL No. :MFCD00082751

Safety of [ 16635-95-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
 

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