Journal of Organic Chemistry p. 5695 - 5699 (1988)
Update date:2022-07-29
Topics:
Baeckvall, Jan-E.
Vaegberg, Jan O.
A mild method for stereo- and regioselective 1,4-dialkoxylation of conjugated dienes was developed.The reaction is catalysed by palladium(II), and p-benzoquinone is used as the oxidant.It was found that the reaction rate depended on the presence of catalytic amounts of a strong acid.The role of the acid is probably 2-fold: (i) to create a cationic (?-allyl)palladium intermediate and (ii) to protonate the oxygen in the coordinated benzoquinone in the (?-allyl)palladium(benzoquinone) intermediate.
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Doi:10.1016/S0040-4020(01)86741-7
(1988)Doi:10.1021/jo00259a006
(1988)Doi:10.1055/s-0032-1317713
(2013)Doi:10.1021/acs.joc.7b02196
(2017)Doi:10.1002/ejoc.200900064
(2009)Doi:10.1016/j.jorganchem.2009.01.036
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