Novel and Efficient Chromium(II)-Mediated Desulfonylation of α‑Sulfonyl Ketone

A novel and efficient method for the Cr­(II)-mediated desulfonylation of α-sulfonyl ketone by a Cr–ligand–Mn system has been developed during the course of process research on Halaven (eribulin mesylate). This reaction is dramatically accelerated in the presence of an appropriate bipyridyl-type liga...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 12; pp. 3158 - 3161
Main Authors Inanaga, Kazato, Fukuyama, Takashi, Kubota, Manabu, Komatsu, Yuki, Chiba, Hiroyuki, Kayano, Akio, Tagami, Katsuya
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 19.06.2015
Subjects
2,2'-Dipyridyl - chemistry
Catalysis
Chromium - chemistry
Furans - chemistry
Ketones - chemistry
Ligands
Manganese - chemistry
Molecular Structure
Sulfhydryl Compounds - chemistry
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Summary:A novel and efficient method for the Cr­(II)-mediated desulfonylation of α-sulfonyl ketone by a Cr–ligand–Mn system has been developed during the course of process research on Halaven (eribulin mesylate). This reaction is dramatically accelerated in the presence of an appropriate bipyridyl-type ligand. This system is applicable to reduction of α-sulfur-substituted ketones. In addition, a Cr–Cp2ZrCl2–Mn catalytic system is also applicable to desulfonylation of α-sulfonyl ketone.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01497