Table 1 Optimization of the thia-Baeyer–Villiger reaction.

From: Post-functionalization of dibenzothiophene to functionalized biphenyls via a photoinduced thia-Baeyer-Villiger oxidation

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Entry

Variations from standard conditions

Yield of BPSa

1

None

86%

2

No light

0b

3

No [TCPPFe]Cl

0c

4

[TCPPMn]Cl instead of [TCPPFe]Cl

trace

5

[TPPFe]Cl instead of [TCPPFe]Cl

39%

6

[T(o-NH2)PPFe]Cl instead of [TCPPFe]Cl

15%

7

[T(o-NO2)PPFe]Cl instead of [TCPPFe]Cl

62%

8

t-BuOOH (2.0 eq)

33%

9

t-BuOOH (4.0 eq)

63%

10

t-BuOOH (8.0 eq)

87%

11

500 W Hg Lamp

63%d

12

150 W Hg Lamp

69%e

13

From DBTO 11a and t-BuOOH (4.0 eq)

84%

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  1. aIsolated yield.
  2. bDBT was recovered in 92% yield.
  3. cNo reaction.
  4. dDBTO2 was isolated in 30% yield.
  5. eDBTO2 was isolated in 21% yield. [TPPFe]Cl: meso-tetraphenylporphinatoiron (III) chloride; [TCPPFe]Cl: (5,10,15,20-Tetrakis(2-chlorophenyl) porphyrinato) iron (III) chloride); [T(o-NH2)PPFe]Cl: (5,10,15,20-Tetrakis(2-amino)porphyrinato) iron (III) chloride); [T(o-NO2)PPFe]Cl: (5,10,15,20-Tetrakis(2-nitro)porphyrinato) iron (III) chloride); [TCPPMn]Cl: (5,10,15,20-Tetrakis(2-chlorophenyl) porphyrinato)manganese (III) chloride.
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