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

作者：Vilanova Conxin; Sanchez Peris Maria; Roldan Steven; Dhotare Bhaskar; Carda Miguel^*; Chattopadhyay Angshuman

来源：Tetrahedron Letters, 2013, 54(48): 6562-6567.

DOI：10.1016/j.tetlet.2013.09.096

• Homoallyl alcohol
• Low valent metal
• Bimetal redox reaction
• Spontaneity
• Aluminium
• Practical viability

Use of aluminium as the reducing metal in spontaneous bimetal redox reaction has been elegantly exploited for allylation/crotylation of aldehydes in wet solvent. Here, low valent tin was prepared in situ by reduction of SnCl2 center dot 2H(2)O with aluminium in THF/water. The resulting low valent tin acted as an efficient mediator for allylation and crotylation of aldehydes (3a-q) producing the corresponding homoallylic alcohols. The efficacy of this procedure was due to its operational simplicity, practical viability, inexpensiveness, good yields of the products and short reaction time.

• 出版日期2013-11-27