77084-89-0

Upstream product

• 110-89-4 piperidine 
• 104-53-0 3-phenyl-propionaldehyde 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 39655-59-9 4-(3-phenyl-1-propen-1-yl)-morpholine 

Downstream Products

• 85665-54-9 3,5-dibenzylpyridine 
• 104-55-2 3-phenyl-propenal 
• 104-53-0 3-phenyl-propionaldehyde 
• 39655-59-9 4-(3-phenyl-1-propen-1-yl)-morpholine 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed C(sp2)-H Functionalization of Cyclobutenes. Access to Cyclobuta[ c]pyridones and -pyridines

O-(ω-Alkynyl) hydroxamates derived from cyclobutenyl carboxylic acids were identified as viable substrates in intramolecular rhodium(III)-catalyzed heteroannulations, which led to diversely substituted cyclobuta[c]pyridones. Further functionalization of the resulting cyclobutapyridones enabled the synthesis of cyclobuta[c]pyridines and other nitrogen heterocycles after electrocyclic ring opening of the four-membered ring.

Dynamic Covalent Chemistry of Aldehyde Enamines: BiIII- and ScIII-Catalysis of Amine–Enamine Exchange

The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)3 and Sc(OTf)3 (2 mol %) and the equilibria (60 mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with 2 % by-product formation within one week after complete equilibration. This study expands the scope of dynamic C?N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.

Calix[4]arene-diphosphite rhodium complexes in solvent-free hydroaminovinylation of olefins

Under solvent-free conditions rhodium complexes containing hemispherical diphosphites based on a calix[4]arene skeleton catalyse efficiently the hydroaminovinylation of α-olefins, thereby leading to high proportions of linear enamines/amines (when startin

Highly regioselective hydroformylation with hemispherical chelators

The hemispherical diphosphites (R,R)- or (S,S)-5,11,17,23-tetratert-butyl- 25,27-di(OR)-26,28-bis(1,1′-binaphthyl-2,2′-dioxyphosphanyloxy) -calix[4]arene (R = OPr, OCH2Ph, OCH2-naphtyl, O-fluorenyl; R = H, R' = OPr) (LR), all with C2 symmetry, have been synthesised starting from the appropriate di-O-alkylated calix[4]-arene precursor. In the presence of [Rh(acac)(CO)2], these ligands straightforwardly provide chelate complexes in which the metal centre sits in a molecular pocket defined by two naphthyl planes related by the C 2 axis and the two apically situated R groups. Hydroformylation of octene with the LPr/Rh system turned out to be highly regioselective, the linear-to-branched (l:b) aldehyde ratio reaching 58:1. The l:b ratio significantly increased when the propyl groups were replaced by -CH 2Ph (l:b = 80) or -CH2naphthyl (1:b = 100) groups, that is, with substituents able to sterically interact with the apical metal sites, but without inducing an opening of the cleft nesting the catalytic centre. The trend to preferentially form the aldehyde the shape of which fits with the shape of the catalytic pocket was further confirmed in the hydroformylation of styrene, for which, in contrast to catalysis with conventional diphosphanes, the linear aldehyde was the major product (up to ca. 75 % linear aldehyde). In the hydroformylation of frarts-2-octene with the Lbenzyl/ Rh system, combined isomerisation/hydroformylation led to a remarkably high 1:b aldehyde ratios of 25, thus showing that isomerisation is more effective than hydroformylation. Unusually large amounts of linear products were also observed with all the above diphosphites in the tandem hydroformylation/amination of styrene (1:b of ca. 3:1) as well as in the hydroformylation of allyl benzyl ether (1:b ratio up to 20).

A mild oxidation of aldehydes to α,β-unsaturated aldehydes

Phenylselenenyl chloride reacts with enamines at -110° C to give α-phenylselenoaldehydes, and oxidative elimination yields α,β-unsaturated aldehydes.