Application In Synthesis of 1-Bromoundecane. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1-Bromoundecane, is researched, Molecular C11H23Br, CAS is 693-67-4, about Catalytic Asymmetric Fluorination of Copper Carbene Complexes: Preparative Advances and a Mechanistic Rationale. Author is Buchsteiner, Michael; Martinez-Rodriguez, Luis; Jerabek, Paul; Pozo, Iago; Patzer, Michael; Noethling, Nils; Lehmann, Christian W.; Fuerstner, Alois.
The Cu-catalyzed reaction of substituted α-diazoesters with fluoride gives α-fluoroesters with ee values of up to 95%, provided that chiral indane-derived bis(oxazoline) ligands were used that carry bulky benzyl substituents at the bridge and moderately bulky iso-Pr groups on their core. The apparently homogeneous solution of CsF in C6F6/hexafluoroisopropanol (HFIP) is the best reaction medium, but CsF in the biphasic mixture CH2Cl2/HFIP also provides good results. DFT studies suggest that fluoride initially attacks the Cu- rather than the C-atom of the transient donor/acceptor carbene intermediate. This unusual step is followed by 1,2-fluoride shift; for this migratory insertion to occur, the carbene must rotate about the Cu-C bond to ensure orbital overlap. The directionality of this rotatory movement within the C2-sym. binding site determines the sense of induction. This model is in excellent accord with the absolute configuration of the resulting product as determined by x-ray diffraction using single crystals of this a priori wax-like material grown by capillary crystallization
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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem