732
Synlett
G. Chen et al.
Letter
References and Notes
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(
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To a suspension of N,N-dialkylanilines (0.5 mmol, 10 equiv),
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3
(
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2
3
mg, 0.075 mmol, 1.5 equiv) in toluene (0.25 mL) were added
Rh (oct) (1.9 mg, 0.05 equiv) at room temperature. After being
2
4
stirred for 12 h, the reaction was quenched by addition of water
and extracted with EtOAc. The organic layer was washed with
brine and dried over Na SO , filtered, and concentrated. The
3
(
8) Cu-nitrene-mediated C(sp )–H amidation of N-methylaniline
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Wang, L.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. J. Org. Chem. 2008, 73,
2
4
1
yields of the aminated product 2 were determined by H NMR
analysis using 1,3-dinitrobenzene as internal standard. The
residue was purified by preparative TLC purification to afford
the aminated product 2.
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Trichloroethyl{[methyl(phenyl)amino]methyl}carbamate
(
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(
2aa)
1
Colorless oil. H NMR (400 MHz, CDCl , 323 K): = 7.29–7.25
3
(m, 2 H), 6.84–6.81 (m, 3 H), 5.41 (br s, 1 H), 4.91 (d, J = 6.0 Hz, 2
13
H), 4.73 (s, 2 H), 3.01 (s, 3 H). C NMR (100 MHz, CDCl ): =
1
3
cm
3
54.9, 147.7 129.6, 118.7, 113.6, 95.5, 74.6, 59.6, 37.8. IR (neat):
326, 2952, 1722, 1598, 1499, 1367, 1220, 1132, 1041, 817, 750
(e) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem.
–1
+
+
. HRMS-ESI : m/z calcd for C11H13Cl N O [M + H] :
3 2 2
311.0115; found: 311.0115.
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2020. Thieme. All rights reserved. Synlett 2021, 32, 728–732