Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of amines
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Recent Literature
Carbamates and sulfonamides serve as directing groups in Ni-catalyzed asymmetric
Suzuki reactions for cross-coupling of unactivated alkyl electrophiles. Racemic
secondary bromides and chlorides undergo C-C bond formation in a
stereoconvergent process in good ee at room temperature in the presence of a
commercially available Ni complex and chiral ligand.
A. Wilsily, F. Tramutola, N. A. Owston, G. C. Fu, J. Am. Chem. Soc., 2012,
134, 5794-5797.
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.
A unique
combination of organic catalysts promotes the transfer of electrons and
hydrogen atoms in a mild, modular, and practical direct hydroarylation of vinyl amine
derivatives with a wide range of aryl halides (including aryl chlorides). This
general and highly chemoselective protocol delivers a broad range of
arylethylamine products with complete regiocontrol.
A. J. Boyington, C. P. Seath, A. M. Zearfoss, Z. Xu, N. T. Jui, J. Am. Chem. Soc.,
2019,
141, 4147-4153.
Transition-metal-free catalysis enables the opening of aziridines and azetidines
using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts to provide β,β-
and γ,γ-substituted amines with complete regioselectivity and high
diastereoselectivity.
T. Liu, Y. Li, L. Lai, J. Cheng, J. Sun, J. Wu, Org. Lett.,
2018, 20, 3605-3608.
N-heterocyclic carbene (NHC) ligands efficiently promote a palladium-catalyzed
stereospecific and regioselective cross-coupling of enantiopure 2-arylaziridines
with arylboronic acids under mild conditions without β-hydride elimination to
construct a tertiary stereogenic center.
Y. Takeda, Y. Ikeda, A. Kuroda, S. Tanaka, S. Minataka, J. Am. Chem. Soc., 2014,
136, 8544-8547.
A cross-coupling reaction between N-sulfonyl aziridines and organozinc
reagents is possible under mild and functional-group-tolerant conditions in the
presence of inexpensive and air-stable Ni(II) source and dimethyl fumarate as
ligand to yield β-substituted amines. The stereoselectivity of the reaction is
consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C
bond formation.
C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2012,
134, 9541-9544.
A nickel-catalyzed reductive cross-coupling of aziridines and allylic
chlorides in the presence of manganese metal as the reducing agent affords
β-allyl-substituted arylethylamines bearing various functional groups. The
utility of this reaction was also demonstrated by scale-up preparation and
diverse transformations, including the synthesis of Baclofen and several
bioactive molecular motifs.
S. Liu, S.-L. Wang, J. Wan, S. Peng, J.-R. Zhang, H.-J. Ding, B. Zhang, H.-L.
Ni, P. Cao, P. Hu, B.-Q. Wang, B. Chen, Org. Lett., 2023, 25,
6582-6586.
A highly efficient asymmetric intermolecular Ni-catalyzed reductive
dicarbofunctionalization of vinyl amides, vinyl boranes, or vinyl phosphonates
with two distinct readily available electrophiles, namely, Csp2- and
Csp3-halides, provides chiral products in a highly regio- and
enantioselective manner.
X. Wei, W. Shu, A. García-Domínguez, E. Merino, C. Nevado, J. Am. Chem. Soc.,
2020, 142, 13515-13522.
A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines
delivers valuable β-substituted phenethylamines via a challenging reductive
elimination that affords a quaternary carbon. An electron-deficient olefin
ligand is crucial for achieving high rates and chemoselectivity for C-C bond
formation over β-H elimination.
C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2015,
137, 5638-5641.
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.