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COMMUNICATION
Journal Name
version to 1 with acetic formic anhydride. Furthermore, it was
demonstrated that CO2 can be transformed to a bench-stable
CO surrogate in a single operation. With this proof-of-principle
in hand, we are currently trying to develop a tandem proce-
dure for the CO2 utilization.
ACS Catal., 2014, 4, 1706.
DOI: 10.1039/C5CC05012J
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Table 3 Methoxy- or benzyloxycarbonylation of various olefins.a
5
AcO
MeO2C
11
21, 22
12
23
46% (<1:>99)b
0.75 mol-% [Pd]: 51% (<1:>99)b
32% (>99:<1)b
1.0 mol-% [Pd]: 43% (>99:<1)b
6
7
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14
24
13
24
29% (50:50)c
0.75 mol-% [Pd]: 39% (50:50)c, d
O
N
O
8
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15
25
16
26
47% (46:54)
34% (<1:>99)
0.75 mol-% [Pd]: 34% (<1:>99)d, e
1.0 mol-% [Pd]: 82% (46:54)
17
27, 28
53% (<1:>99)
1.0 mol-% [Pd]: 91% (<1:>99)b, e
18
27, 28
39% (<1:>99)
1.0 mol-% [Pd]: 89% (<1:>99)b, e
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(CH2)6CH3
(CH2)6CO2Me
19
29
20
30
16% (<1:>99)
11% (<1:>99)d
a
Reaction conditions: Chamber A: CO generation (max 2.5 bar): 1 (2.13 mmol,
449 mg), Na2CO3 (3.19 mmol, 340 mg) in DMF (1 mL); Chamber B: alkene
(1.00 mmol, 1 M solution), 1:3 MeOH:DCM (v/v), 0.5 mol% Pd(dba)2 (5.0 µmol,
2.9 mg), 2 mol% dtbpx (20 µmol, 7.9 mg), 7.5 mol% rac-BNPA (75 µmol, 26 mg),
RT, 14 h. Isolated yields are given; the bracketed values refer to regioselectivities
b
(b:l) measured by GC-FID analysis of the crude reaction mixture.
With
BnOH:Solvent (1:3). c Regioisomer ratios refer to the benzylic and terminal ester,
respectively. d 0.75 mmol alkene. e 50 °C, DCE as solvent.
Notes and references
Acknowledgement: We thank the Fonds der Chemischen Industrie
(Liebig Fellowship I.F.) and the University of Regensburg for the support.
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4 | J. Name., 2012, 00, 1-3
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