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Aromatic Dehalogenation [ BER - Ni(OAc)2 ]

Started by foxy2, November 27, 2001, 11:29:00 PM

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foxy2

Facile reduction of aryl halides with borohydride exchange resin-nickel acetate.    

Bull. Korean Chem. Soc. 14(5), 543-5 (1993)

(http://journal.kcsnet.or.kr/publi/bul/bu93n5/543.pdf

Abstract

Redn. of aryl halides with borohydride exchange resin (BER) in the presence of Ni(OAc)2 in MeOH proceeded in good yield with excellent selectivity.  Thus, redn. of 4-ClC6H4CH2OH with BER-Ni(OAc)2 in MeOH gave 87% PhCH2OH. 

Further Reading: Post 381478 (not existing)

Rhodium

Preparation of Borohydride Exchange Resin
J. Org. Chem. 59, 4687 (1994)

An aqueous solution of sodium borohydride (1 M, 1 L) was stirred with wet chloride-form anion exchange resin (Amberlite IRA-400 (20-50 mesh), 200g) for 1 h. The resulting resin was washed thoroughly with distilled water until free from excess NaBH4. The borohydride form anion exchange resin was then dried in vacuo at 60°C for 5 h. The dried resin was analyzed for borohydride content by hydrogen evolution on acidification with 2 N HCl, and the average hydride content of BER was found to be 3.3 mmol of BH4- per gram. The dried resin was stored under nitrogen in refrigerator (-4°C). The hydride content was constant over 6 weeks.

References:
Yoon, N. M; Tetrahedron Lett. 24, 5367 (1983)
Kabalka, G; Synth. Commun.  20, 293 (1990) and references cited therein.