Categories: C-C Bond Formation > Nitrogen-containing molecules >

Synthesis of amines

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Recent Literature

Palladium-catalyzed reductive cross-coupling reaction of various protected allylic amine derivatives with alkylzinc reagents yields anti-Markovnikov products. Preliminary mechanistic studies suggest that a reversible β-hydride elimination/hydride insertion process furnishes the primary Pd-alkyl intermediate, which then undergoes transmetalation followed by reductive elimination.
R. J. DeLuca, M. S. Sigman, J. Am. Chem. Soc., 2011, 133, 11454-11457.

In stereoconvergent, arylamine-directed alkyl-alkyl Suzuki cross-coupling reactions, structure-enantioselectivity studies are consistent with the nitrogen, not the aromatic ring, serving as the primary site of coordination of the arylamine to the catalyst.
Z. Lu, A. Wilsily, G. C. Fu, J. Am. Chem. Soc., 2011, 133, 8154-8157.

Transition metal carbenes can directly be generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and can be used in a highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes to access various β-chiral sulfonamides.
S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc., 2011, 133, 10352-10355.