A practical procedure of low valent tin mediated Barbier allylation of aldehydes in wet solvent

Synthesis of active tin: an efficient reagent for allylation reaction of carbonyl compounds

“…Among the various types of Grignard-Barbier reactions, the carbonyl allylation reaction via organotin, like alkali and alkaline-earth metal counterparts, is a useful reaction for the synthesis of homoallylic alcohols which are important synthons for many useful compounds in organic and pharmaceutical industries. 22,28 We have tested the catalytic activity of Sn(0) material towards carbonyl allylation reaction. For the model study we employed 4-chloro benzaldehyde as an electrophile.…”

“…21 A. Chattopadhyay and co-workers reported the synthesis of homoallylic alcohol using SnCl 2 and aluminium metal in organic solvent (THF). 22 However all these reported methods were carried out under harsh reaction conditions, or using organic solvents or with multiple reagents. Hence, simplification of allylation reaction using a simple and effective catalyst or reagent and green solvents under mild reaction conditions is highly desirable.…”

Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes

“…但是, 继续延长反应时 间到 6～10 h 时, 收率变化不大(表 3, Entries 4～6). 当 反应时间增加到 12 h 时 , 反应收率只是略提高为 78%(表 3, Entry 7), 所以, 确定 4 [5,14] . 糠醛也有较好的 75%收率(表 6, Entry 8), 但是与异丁醛相比则下降较多, 可能是因为杂环上氧原 子的对金属催化剂的影响.…”