Indium-copper and indium-silver mediated barbier-grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water.
An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I(2) or In/AgI/I(2) system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I(2) were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.
Shen
Zhi-Liang
ZL
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
Yeo
Yan-Lin
YL
Loh
Teck-Peng
TP
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000438:Alcohols; D000447:Aldehydes; D006846:Hydrocarbons, Halogenated; D007204:Indium; D014867:Water; D012834:Silver; D003300:Copper