Abstract
A novel mediator (Sn/I2) has been developed and employed in the allylation and crotylation of various aldehydes and ketones with allyl (crotyl) halide in water. With a catalytic amount of I2 and less than stoichiometric amounts of Sn, allyl (crotyl) bromide reacts with carbonyl compounds to produce the corresponding alcohols in quantitative yield. Even the inert allyl chloride and crotyl chloride can react with aldehydes to give the corresponding alcohols. The diastereoselectivity and regioseletivity of the reaction have also been studied. Sn/I2 mediated allylations of aldehydes with crotyl bromide produced dominant γ-adducts with minor α-isomers while Sn/I2 mediated allylations of aldehydes with crotyl chloride afforded dominant α-adducts with minor γ-isomers.
Highlights
Organic reactions in aqueous media is a significant branch of green chemistry utilizing a variety of organometallic reagents to accomplish Barbier-type carbonyl allylation in water.[1]
Even allyl chloride and crotyl chloride, which were inert to allylation in most cases, can be activated in the ISSN 1551-7012
Regioselectivity of the allylation can be achieved to some extent under the condition
Summary
Organic reactions in aqueous media is a significant branch of green chemistry utilizing a variety of organometallic reagents to accomplish Barbier-type carbonyl allylation in water.[1]. Of tin was employed as a mediator, the allylation can be carried out smoothly at room temperature to give rise to the corresponding product with a high yield (Table 2).
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