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. 2021 Jan 18;11(6):3539–3546. doi: 10.1039/d0ra10739e

Substrate scope of the cobalt-catalysed Giese reaction of alkyl tosylates with activated olefinse.

graphic file with name d0ra10739e-u2.jpg
a

Reaction conditions: alkyl tosylate (0.25 mmol), activated olefin (0.375 mmol), vitamin B12 (12.5 μmol, 5 mol%), Et3N·HCl (0.38 mmol), Mn powder (0.75 mmol), DMF (1.5 mL); room temperature for 16 h; the blue-light irradiation; argon atmosphere. Isolated yield.

b

The reaction was conducted with 5-phenylpenthyl tosylate (5 mmol) and phenyl acrylate (7.5 mmol).

c

5-(tert-Butyldimethylsilyl)-1-chloropenthane was used instead of the corresponding tosylate.

d

Reaction time: 24 h.

e

10 mol% of vitamin B12 was used.

f

Co(TMPP) was used instead of vitamin B12.

g

Diastereomeric alkyl tosylate [65 : 35] was used. The values in bracket indicate a diastereomeric ratio of the radical adduct.

h

See main text.