Table 1 Optimization of the reaction conditionsa.

From: Migratory functionalization of unactivated alkyl bromides for construction of all-carbon quaternary centers via transposed tert-C-radicals

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Entry

Ligand

Solvent

Yieldb

rrc

1

L1

DMA

64

>20:1

2

L2

DMA

72

>20:1

3

L3

DMA

70

>20:1

4

L4

DMA

54

>20:1

5

L5

DMA

62

>20:1

6

L6

DMA

62

6:1

7

L7

DMA

n.r.

8

L8

DMA

n.r.

9

L9

DMA

n.r.

10

L2

DMSO

44

1:1

11

L2

1,4-Dioxane

n.r.

12

L2

THF

89d

>20:1

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  1. aUnless otherwise noted, reactions were carried out with 1a (0.6 mmol), 2a (0.2 mmol), Ni salt (0.01 mmol), ligand (0.012 mmol), Mn powder (0.3 mmol) in DMA (2.0 mL) under a nitrogen atmosphere at room temperature for 12 h.
  2. bAssay yields determined by 19F NMR with 1-iodo-4-(trifluoromethyl)benzene as internal standard.
  3. cRr refers to the ratio of desired product to the sum of all the other regioisomers, as determined by the 19F NMR analysis of the crude products.
  4. dIsolated yields.