Ti-Mediated Efficient Reductive Dehalogenation of Carbon-Halogen Bonds

A mild and efficient methodology for the reductive dehalogenation of carbon-halogen bonds in both activated (allylic or benzylic) and non-activated halides with excess Ti-III is thoroughly described. A detailed computational and experimental study corroborates that the reaction occurs via the allyl(...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 5; no. 8; pp. 991 - 1001
Main Authors Gonzalez-Delgado, Jose A., Prieto, Consuelo, Enriquez, Lourdes, Jaraiz, Martin, Lopez-Perez, Jose L., Barrero, Alejandro F., Arteaga, Jesus F.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.08.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
chemoselectivity
TITANOCENE DICHLORIDE
ASYMMETRIC-SYNTHESIS
HYDROGEN-ATOM TRANSFER
LITHIUM TRIETHYLBOROHYDRIDE
computational calculations
titanium
ALKYL-HALIDES
ALLYLIC HALIDES
SELECTIVE REDUCTIONS
RADICAL CYCLIZATIONS
ORGANIC HALIDES
reduction
dehalogenation
EXCEPTIONALLY POWERFUL NUCLEOPHILE
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Summary:A mild and efficient methodology for the reductive dehalogenation of carbon-halogen bonds in both activated (allylic or benzylic) and non-activated halides with excess Ti-III is thoroughly described. A detailed computational and experimental study corroborates that the reaction occurs via the allyl(benzyl) radical and allyl(benzyl)-Ti, which is protonated by a BrOnsted acid, and proceeds regioselectively in the case of allylic derivatives. This synthetic method is compatible with a wide range of functional groups and reaction conditions, and thus presents a mild process for reductive dehalogenation in the field of organic synthesis.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201600169