Table 1 Reaction optimization

From: Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenation

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Entry

Ligand

Yield[%]a (3a:4a:5a:6a)

Entry

Ligand

Yield[%]a (3a:4a:5a:6a)

1

PPh3

47 (0/17/25/5)

9

PPhCy2

43 (0/10/29/4)

2

PCy3

41 (0/0/35/6)

10

P(OMe)3

30 (0/14/16/0)

3

PnBu3

39 (0/9/30/0)

11

PnPr3

29 (0/13/16/0)

4

PtBu3

25 (25/0/0/0)

12

PMe2Ph

32 (0/25/7/0)

5

XPhos

35 (35/0/0/0)

13

PtBuCy2

32 (0/15/17/0)

6

PMe3

85 (0/85/0/0)

14

Xantphos

38 (0/16/19/3)

7

PPh2Cy

44 (0/17/22/5)

15b

PCy3

79 (0/0/79/0)

8

DCYPE

0

16b

PnBu3

92 (0/0/92/0)

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  1. Reactions conditions: Ni(cod)2 (10 mol%), ligand (20 mol%), CsOPiv (1.5 equiv), 1a (0.2 mmol), 2a (0.4 mmol), t-AmylOH (1 mL), 70 °C, 48 h
  2. a1H NMR yields with C2H2Br4 as internal standard
  3. bMolar ratio of 1a:2a = 1.5:1
  4. cPnBu3 (20 mol%), H2 scavenger (2.0 equiv). The 1H NMR yield of 5a is given
  5. d1.0 equiv H2 acceptor
  6. eThe isolated yield is given in parenthesis
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