Categories: C-C Bond Formation > Amines, Arenes >
Diarylmethylamines
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Recent Literature
A highly efficient three-component coupling reaction between thioformamides and
organolithium and Grignard reagents was developed. The generality of the process
has been demonstrated by using various combinations of reactants and reagents.
T. Murai, F. Asai, J. Am. Chem. Soc., 2007,
129, 780-781.
A three-component, Ni-catalyzed reductive coupling enables a convergent
synthesis of tertiary benzhydryl amines, which are challenging to access by
traditional reductive amination methodologies. The condensation of secondary
N-trimethylsilyl amines with benzaldehydes provides iminium ions in situ,
which react with several distinct classes of organic electrophiles.
C. Heinz, J. P. Lutz, E. M. Simmons, M. M. Miller, W. R. Ewing, A. G. Doyle, J. Am. Chem. Soc., 2018,
140, 2292-2300.
A Lewis acid palladium-catalyzed reaction of amides, aryl aldehydes, and
arylboronic acids enables a practical and general synthesis of α-substituted
amides from simple, readily available building blocks.
T. Beisel, G. Manolikakes, Org. Lett., 2013,
15, 6046-6049.
Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium
nanoparticles proceeded in aqueous media to afford chiral (diarylmethyl)amines
in high yields with outstanding enantioselectivities. This heterogeneous
catalyst system exhibited very high turnover numbers. The reusability of the
catalyst was also demonstrated.
T. Yasukawa, T. Kuremoto, H. Miyamura, S. Kobayashi, Org. Lett.,
2016, 18, 2716-2718.
A catalyst prepared in situ from Rh(I) and a chiral diene ligand enables a rapid
synthesis of enantiomerically enriched tosyl-protected diarylmethylamines from
arylboronic acids and N-tosylaldimines under mild conditions. This
addition offers access to diarylmethylamines in good yields with excellent
chiral purity at room temperature using MeOH as a solvent and NEt3 as
a base.
C.-C. Chen, B. Gopula, J.-F. Syu, J.-H. Pan T.-S. Kuo, P.-Y. Wu, J. P. Henschke,
H.-L. Wu, J. Org. Chem., 2014,
79, 8077-8085.
A highly efficient asymmetric arylation of N-nosylimines with arylboronic
acids catalyzed by a rhodium-diene complex enables the synthesis of a wide range
of enantiopure N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one
in high yields under very mild conditions.
L. Wang. Z.-Q. Wang, M.-H. Xu, G.-Q. Lin, Synthesis, 2010,
3263-3264.
Monosubstituted C1-symmetric dicyclopentadienes as a new class
of diene ligands enable a rhodium-catalyzed asymmetric arylation of N-tosylarylimines
in excellent yields with high enantioselectivities. The preparation of these
diene ligands relied on an efficient lipase-catalyzed resolution as the key step.
C. Shao, H.-J. Yu, N.-Y. Wu, C.-G. Feng, G.-Q. Lin, Org. Lett., 2010,
12, 3820-3823.
A new type of C2-symmetric chiral diene ligand was applied
successfully in the Rh-catalyzed asymmetric arylation of N-tosylarylimines
with arylboronic acids to give a broad range of highly enantiomerically enriched
diarylmethylamines as well as 3-aryl substituted phthalimidines.
Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc., 2007,
129, 5336-5337.
The use of a new C2-symmetric diene ligand (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene
(Ph-bod*) for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines
with arylboroxines allowed asymmetric synthesis of diarylmethylamines with
high enantioselectivity.
N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc.,
2004, 126, 13584-13585.
P-chiral P,π-hybrid ligands are both sterically and electronically tunable at
the substituents on the phosphorus atom and the π-system of the ligand.
Catalytic asymmetric addition of boronic acids to imines proceeds with high
levels of enantioinduction in the presence of these ligands.
J. D. Sieber, D. Chennamadhavuni, K. R. Fandrick, B. Qu, Z. S. Han, J. Savoie,
S. Ma, L. P. Samankumara, N. Grinberg, H. Lee, J. J. Song, C. H. Senanayake, Org. Lett.,
2014,
16, 5494-5497.
The asymmetric arylation of N-tosylarylimines with arylboronic acids
was realized by using rhodium/(S)-ShiP as catalyst in aqueous toluene
to give diarylmethylamines in good yields and enantioselectivities.
H.-F. Duan, Y.-X. Jia, L-X. Wang, Q.-L. Zhou, Org. Lett.,
2006,
8, 2567-2569.
The asymmetric synthesis of diarylmethyl amines was realized by
rhodium-catalyzed asymmetric addition of aryl titanium reagents to
N-alkylidene sulfonamides.
T. Hayashi, M. Kawai, N. Tokunaga, Angew. Chem., 2004, 116,
6251-6252.
Chiral 2-methoxy-1-naphthylsulfinyl-based phenyl backbone
sulfoxide-olefin ligands enable highly enantioselective Rh-catalyzed additions of arylboronic acids
to N,N-dimethylsulfamoyl-protected aldimines to afford a
broad range of chiral diarylmethylamines in high yields with
excellent enantioselectivities. Moreover, efficient
enantioselective arylation of cyclic N-sulfonylimines was also achieved.
F. Xue, Q. Liu, Y. Zhu, Y. Huang, J. Ge, B. Wan, Synthesis, 2020, 52,
1498-1511.
A chiral bicyclic bridgehead phosphoramidite (briphos) ligand derived from
1-aminoindane was efficient for the Rh-catalyzed enantioselective 1,2-arylation
of N-sulfonyl imines, while that derived from
1,2,3,4-tetrahydro-1-naphthylamine was efficient for 1,4-arylation of
α,β-unsaturated cyclic ketones. For α,β-unsaturated N-tosyl ketimines,
the briphos derived from 1-aminoindane selectively provided γ,γ-diaryl N-tosyl
enamines.
A. Lee, H. Kim, J. Org. Chem.,
2016,
81, 3520-3527.
A selective rhodium/phosphoramidite-catalyzed synthesis of diarylmethyl
amines gave high enantioselectivities and high yields. The small and cheap
N,N-dimethylsulfamoyl protecting group was easily removed by a
microwave-assisted transamination.
R. B. C. Jagt, P. Y. Toullec, D. Geerdink, J. G. de Vries, B. L. Feringa, A.
J. Minnaard, Angew. Chem. Int. Ed., 2006,
45, 2789-2791.