Synthesis and structure of organobismuth chlorides and triflates containing (C,E)-chelating ligands (E=O, S) and their catalytic application in the allylation of aldehydes with tetraallyltin

Nianyuan Tan, Yi Chen, Yongbo Zhou, Chak Tong AU, Shuang Feng Yin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Four air-stable hypervalent organobismuth compounds with (C,O)- or (C,S)-chelating ligands, namely, R2BiCl (R=2-(MeECH 2)C6H4; E=O (3), S (4)), [2-(MeOCH 2)C6H4]2BiOTf (5), and [{2-(MeSCH2)C6H4}2Bi][OTf] (6; OTf=triflate) were successfully synthesized. The structures of compounds 3-6 were determined by single-crystal X-ray diffraction. Compound 6 comprises the [2-(MeSCH2)C6H4]2Bi+ cation and the OTf- anion. Compounds 5 exhibited good catalytic efficiency and reusability for the allylation reaction of different aldehydes with tetraallyltin in methanol to give the corresponding homoallylic alcohols in excellent yields. Hyped up: Four air-stable hypervalent organobismuth compounds with (C,O)- or (C,S)-chelating ligands, R2BiCl (R=2-(MeECH 2)C6H4; E=O, S), [2-(MeOCH2)C 6H4]2BiOSO2CF3 (see picture) and [{2-(MeSCH2)C6H4} 2Bi][OSO2CF3], have successfully been synthesized and characterized. The pictured compound shows excellent catalytic activity and reusability for the allylation of aldehydes with tetraallyltin.

Original languageEnglish
Pages (from-to)1363-1369
Number of pages7
JournalChemPlusChem
Volume78
Issue number11
DOIs
Publication statusPublished - Nov 2013

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • aldehydes
  • allylation
  • bismuth
  • chelates
  • hypervalent compounds

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