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ChemComm
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DOI: 10.1039/C5CC04266F
COMMUNICATION
Journal Name
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Table 3 Oxidation of various benzylic, allylic and aliphatic primary
alcohols catalysed by BT, DI and the control system Phen+TEMPO[a]
Phen+
Substrate
BT
DI
TEMPO
16 (32)
7 (35)[c]
,
10 (20),
6 (30)[c]
>99 (198), 49 (490)[b]
>99 (198), 45 (450)[b]
>99 (198), 42 (420)[b]
>99 (198), 79 (395)[c]
94 (188), 37 (370)[b]
95 (190) [d], 68 (340)[c]
16 (32)
18 (36)
17 (34)
19 (38)
20 (40)
18 (36)
17 (34)
20 (40)
16 (32)
22 (44)
OH
>99 (198)[d]
97 (194)[d], 36 (360)[b][d]
20 (40)
20 (40)
18 (36)
18 (36)
Reactions were performed in dry acetonitrile (0.1 mL) at rt for
3 hrs. with 330 µmol benzyl alcohol, 0.5 mol % catalyst(s), 0.5
mol % [Cu(MeCN)4]OTf and 1 mol % NMI. [a] As determined by
gas chromatography. [b] 0.1 mol % catalyst, 12 hrs (unless it is
in combination with (d), then the reaction time was 24 hrs). [c]
0.2 mol % catalyst, 12 hrs. (unless it is in combination with (d),
then the reaction time was 24 hrs). [d] Air balloon, 24 hrs.
groups on the peptoid scaffold. These features enabled to
develop a very active Cu-TEPMO based catalyst for the aerobic
oxidation of primary alcohols, operating in loading of 0.1 mol%
with high TON. Based on their inherent modularity, peptoids
hold great potential as intramolecular cooperative catalysts for
highly efficient chemical reactions, including asymmetric
transformations, by simply incorporating various catalytic and
non-catalytic groups (e.g. chiral) in their sequence.
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4 | J. Name., 2012, 00, 1-3
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