Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1-Boc-4-(Aminomethyl)piperidine, is researched, Molecular C11H22N2O2, CAS is 144222-22-0, about Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines.Product Details of 144222-22-0.
Herein, a reliable method for accessing α-branched amines RNHCH(R1)(CH2)2R2 (R = (4-methylphenyl)sulfonyl, (2,4,6-trimethylphenyl)sulfonyl; R1 = Ph, 4-morpholinophenyl, furan-2-yl, etc.; R2 = Ph, 3-fluorophenyl, 9H-fluoren-2-yl, etc.) via nickel-catalyzed hydroalkylation reactions was reported. Specifically, by using bis(cyclooctadiene)nickel (Ni(cod)2) together with a phosphine ligand, a formal C(sp3)-H bond insertion reaction between olefins CH2=CHR2 and N-sulfonyl amines RNHCH2R1 without the need for an external hydride source was achieved. The amine not only provides the alkyl motif but also delivers hydride to the olefin by means of a nickel-engaged β-hydride elimination/reductive elimination process. This method provides a platform for constructing chiral α-branched amines (R/S)-RNHCH(R1)CH2CH2R2 by using a P-chiral ligand, demonstrating its potential utility in organic synthesis. Notably, a sulfonamidyl boronate complex formed in situ under basic conditions promotes ring-opening of the azanickellacycle reaction intermediate, leading to a significant improvement of the catalytic efficiency.
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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem