Neodymium-Promoted Highly Selective Carbon-Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

The carbon-carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly alpha-regioselective and was conveniently carried out under mild conditions in a one-pot fashi...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 52; no. 22; pp. 3446 - 3451
Main Authors Xie, Dengbing, Wang, Yiqiong, Yang, Bo, Zhang, Songlin
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.11.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NEW-GENERATION METHOD
LANTHANUM METAL
ORGANIC-SYNTHESIS
ALKENE SYNTHESIS
one-pot reaction
DIIODIDE
CROSS-COUPLING REACTIONS
Barbier-type reaction
ELECTRON-TRANSFER
REDUCTION
BARBIER REACTION
SAMARIUM(II)
diethyl phosphite
alpha-regioselective
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Summary:The carbon-carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly alpha-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1707219