Atom-economical brominations with tribromide complexes in the presence of oxidants

Yubata, Kotaro; Matsubara, Hiroshi

doi:10.1016/j.tetlet.2019.03.011

Cited by 5 publications

(2 citation statements)

References 14 publications

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“…The 1,2-dichloride compound 52, bearing a reactive benzylic tertiary C−Cl bond, was prepared in good yield from α-methylstyrene. Several other activated alkenes, such as the silyl-and ester-substituted alkenes, also proved to be viable substrates to deliver the dichloride products (53)(54)(55)(56), in particular, methyl cinnamate was converted to the 1,2-dichloride 56 in an excellent d.r. ratio (> 19:1).…”

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confidence: 99%

“…The 1,2dichloride compound 52, bearing a reactive benzylic tertiary C−Cl bond, was prepared in good yield from a-methylstyrene. Several other activated alkenes, such as the silyl-and estersubstituted alkenes, also proved to be viable substrates to deliver the dichloride products (53)(54)(55)(56), in particular, methyl cinnamate was converted to the 1,2-dichloride 56 in an excellent diastereomeric ratio (>19:1). To our delight, preliminary experiments showed that this protocol can be readily extended to the 1,2-chlorothiolation transfer reaction using the commercially available 2-chloroethyl phenyl sulfide (10 equivalents) as the donor (Fig.…”

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Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations

Dong

Roeckl

Waldvogel

et al. 2021

Science

173

113

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Vicinal dibromides and dichlorides are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that are traditionally synthesized using hazardous elemental chlorine and bromine. Meanwhile, the environmental persistence of halogenated pollutants necessitates improved approaches to accelerate their remediation. Here, we introduce an electrochemically assisted shuttle (e-shuttle) paradigm for the facile and scalable interconversion of alkenes and vicinal dihalides, a class of reactions that can be used both to synthesize useful dihalogenated molecules from simple alkenes and to recycle waste material through retro-dihalogenation. The reaction is demonstrated using 1,2-dibromoethane, as well as 1,1,1,2-tetrachloroethane or 1,2-dichloroethane, to dibrominate or dichlorinate, respectively, a wide range of alkenes in a simple setup with inexpensive graphite electrodes. Conversely, the hexachlorinated persistent pollutant lindane could be fully dechlorinated to benzene in soil samples using simple alkene acceptors.

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