Efficient and Convenient Reduction of Organic Carbonyl Compounds to their Corresponding Alcohols by Zn(BH4)2/Charcoal in THF
Author(s) -
Davood Setamdideh,
Mehdi Rahmatollahzadeh
Publication year - 2017
Publication title -
journal of the mexican chemical society
Language(s) - English
Resource type - Journals
ISSN - 2594-0317
DOI - 10.29356/jmcs.v56i2.317
Subject(s) - chemistry , allylic rearrangement , conjugated system , regioselectivity , charcoal , ketone , organic chemistry , aldehyde , carbonyl group , alcohol , reducing agent , medicinal chemistry , catalysis , polymer
Zn(BH4)2 (0.5-1.5 mmol) in the presence of charcoal (1 mmol) reduces a variety of organic carbonyl compounds such as al- dehydes, ketones, acyloins, α-diketones and α,β-unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in THF at room temperature in high to excellent yields. The chemoselective reduction of aldehydes over ketones was successfully accomplished with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols was also performed in in high to excellent yields with this reducing system. Resumen. Los compuestos carbonilicos como aldehidos, cetonas, aci- loinas, α-dicetonas y compuestos carbonilicos α,β-insaturados se redu- cen con Zn(BH4)2 (0.5-1.5 mmol) conteniendo carbon (1 mmol) a los alcoholes correspondientes. Este sistema reductor permite la reduccion quimioselectiva de aldehidos en presencia de cetonas y la reduccion regioselectiva de compuestos carbonilicos insaturados a los alcohols alilicos correspondientes con rendimientos de buenos a excelentes. Palabras clave: Zn(BH4)2, reduccion, compuestos carbonilicos, car- bon, quimioselectividad, regioselectividad.
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