Table 1 Condition optimizationa

From: Ketones from aldehydes via alkyl C(sp3)−H functionalization under photoredox cooperative NHC/palladium catalysis

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Entry

preNHC

[Pd]

Ligand

3ab (%)

4ac (%)

1

N1

Pd(OAc)2

L1

24

29

2

N2

Pd(OAc)2

L1

37

0

3

N3

Pd(OAc)2

L1

13

15

4

N2

Pd(OAc)2

L2

26

0

5

N2

Pd(OAc)2

L3

67(69d)

0

6

N2

Pd(PPh3)4

L3

39

0

7

N2

Pd(TFA)2

L3

19

14

8

N2

PdCl2

L3

17

19

9

N2e

Pd(OAc)2

L2

13

0

10

N2

Pd(OAc)2f

L3

29

19

11

N2

Pd(OAc)2

L3g

20

11

12h

N2

Pd(OAc)2

L3

29

0

13

/

Pd(OAc)2

L3

0

/

14

N2

/

L3

0

/

15i

N2

Pd(OAc)2

L3

0

/

  1. aReaction conditions: 1a (0.1 mmol), 2a (1.5 equiv.), [Pd] (10 mol%), Ligand (20 mol%), preNHC (20 mol%), Cs2CO3 (2.0 equiv.), 1.0 mL PhCF3, 36 W Blue LEDs, r.t., under N2.
  2. bYields of 3a determined by 1H NMR using CH2Br2 as standard.
  3. cYields of 4a determined by 1H NMR using CH2Br2 as standard.
  4. dIsolated yields.
  5. e10 mol% of preNHC was used.
  6. f5 mol% of Pd(OAc)2 was used.
  7. g10 mol% of L3 was used.
  8. h36w White LEDs.
  9. iIn dark. r.t. = room temperature.