Table 1 Reaction optimization

From: Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control

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Entries

Ru-catalyst

Acid

Additive

Yield 3a / 3a’ a

1

[Ru(p-cymene)Cl2]2

A1

none

0% / 0%

2

Ru(p-cymene)(OPiv)2

A1

none

0% / 0%

3

[Ru(p-cymene)Cl2]2

A1

NaI (30 %)

0% / 0%

4

Ru(p-cymene)(OPiv)2

A1

NaI (30 %)

0% / 0%

5

RuBnN

A1

NaI (30 %)

27% / trace

6

RuBnN

A1

NaI (30 %)

19% / 25% b

7

Ru(PPh3)3Cl2

A1

NaI (30 %)

15% / 5%

8

Ru(PPh3)3Cl2

A2

NaI (30 %)

15% / 0%

9

Ru(PPh3)3Cl2

A3

NaI (30 %)

48% / 0%

10

Ru(PPh3)3Cl2

A4

NaI (30 %)

50% / 0%

11

Ru(PPh3)3Cl2

A4

NaI (30 %)

62% / 0% c

12

Ru(PPh3)3Cl2

A4

NaI (100 %)

68% / 0% c

13

Ru(PPh3)3Cl2

A4

NaI (100 %)

75% / 0% c,d,e

14

Ru(PPh3)3Cl2

A4

nBu4NI (100 %)

73% / 0% c,d

15

Ru(PPh3)3Cl2

A4

NaBr (100 %)

46% / 0% c,d

16

Ru(PPh3)3Cl2

A4

NaCl (100 %)

19% / 0% c,d

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  1. aYield measured by NMR using 1,3,5-trimethoxybenzene as internal standard.
  2. bMeOH (0.4 M of 1a) used as the solvent.
  3. cRun at 1.3 M concentration of 1a.
  4. dReaction was run at 70 oC.
  5. eIsolated yield.
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