Tetrahedron Letters p. 6561 - 6564 (1997)
Update date:2022-08-11
Topics:
Yang, Cangming
Pittman Jr., Charles U.
Dechlorination of 4-chlorobiphenyl with NaBH4 in high boiling inert solvents from 120-310°C were studied. Complete dechlorination occurred in NaBH4/tetraglyme at 310°C in one hour. Adding LiCl to NaBH4 promoted dechlorination in di-, tri, and tetraglyme respectively at 120-135°C. The rate was significantly enhanced when NaBH4, LiCl, and glyme were prestirred at room temperature for 20 minutes before heating to 120-135°C. At equivalent conditions, dechlorination rates followed the order: tetraglyme > triglyme > diglyme. 4-Chlorobiphenyl dechlorination failed using NaBH4/diphenyl ether. In pentamethyldiethylenetriamine 3- and 4-N,N-dimethylaminobiphenyl was produced through a benzyne intermediate.
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