Table 1 Optimization of reaction conditionsa

From: Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis

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Entry

Deviation from standard conditions

Yield (%)b

1

None

83 (77c)

2

PC-II instead of PC-I

29

3

PC-III instead of PC-I

31

4

PC-IV instead of PC-I

NR

5

NHC B instead of NHC A

NR

6

NHC C instead of NHC A

<5

7

NHC D instead of NHC A

45

8

NHC E instead of NHC A

NR

9

NHC F instead of NHC A

<5

10

MeCN instead of DCM

27

11

THF instead of DCM

NR

12

HAT-2–HAT-5

0–31

13

nBu4NOAc instead of K3PO4

36

14

Cs2CO3 instead of K3PO4

27

15

DBU instead of K3PO4

19

16

NaHCO3 instead of Cs2CO3

30

17

K3PO4 instead of Cs2CO3

27

18

No PC

NR

19

No NHC

NR

20

No base

NR

21

No HAT

NR

22

No light

NR

  1. NR, no reaction.
  2. aStandard conditions: 1a (0.3 mmol), 2a (0.6 mmol), NHC A catalyst (0.06 mmol), photocatalyst (0.003 mmol), Cs2CO3 (0.06 mmol), K3PO4 (0.06 mmol), and HAT-1 catalyst (0.06 mmol) in DCM (4 mL) were irradiated with blue LEDs under Ar at room temperature.
  3. bDetermined by 1H NMR spectroscopy with dibromomethane as an internal standard.
  4. cIsolated yield.