Iron(III) chloride-catalysed direct nucleophilic alpha-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols.
A general and efficient direct method for the alpha-substitution of Morita-Baylis-Hillman alcohols with carbon- and heteroatom-centred nucleophiles such as alcohols, arenes, 1,3-dicarbonyl compounds, and thiols in the presence of FeCl3.6H2O as catalyst has been developed. The reaction is operationally straightforward, accomplished in good to excellent product yields (40-99%) and with exclusive alpha-regioselectivity under mild conditions that did not need an inert and moisture-free environment.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
Xiaoxiang
X
Zhang
Weidong
W
Rao
Sally
S
Chan
Philip Wai Hong
PW
Chan
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides; D005290:Ferric Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000438:Alcohols; D002712:Chlorides; D005290:Ferric Compounds; D006841:Hydrocarbons, Aromatic; D007659:Ketones; D013438:Sulfhydryl Compounds; C024555:ferric chloride