Exceptionally active yttrium-salen complexes for the catalyzed ring opening of epoxides by TMSCN and TMSN3

Biswajit Saha, Mei Huey Lin, T. V. RajanBabu

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

(Chemical Equation Presented) Halide or alkoxide free yttrium-salen complexes are excellent catalysts for the ring opening of epoxides mediated by TMSCN and TMSN3. Substrate to catalyst ratios up to 10000 have been realized in these potentially useful reactions, which can be run under solvent-free conditions. Even though the enantioselectivities for the TMSCN-mediated reaction remains modest (best 77% ee), these studies with a highly tunable ligand system may provide further impetus for work in this important area of catalysis. Even though attempts to isolate a Y-cyanide complex, which was detected by in situ IR spectroscopy, failed, a related dimeric hydroxide complex was isolated. A kinetic study using in situ IR spectroscopy did not provide conclusive data to assign an order with respect to Y in this reaction.

Original languageEnglish
Pages (from-to)8648-8655
Number of pages8
JournalJournal of Organic Chemistry
Volume72
Issue number23
DOIs
Publication statusPublished - 2007 Nov 9

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Yttrium
Epoxy Compounds
Infrared spectroscopy
Catalysts
Enantioselectivity
Cyanides
Catalysis
Ligands
Kinetics
Substrates
trimethylsilyl cyanide
disalicylaldehyde ethylenediamine
hydroxide ion

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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abstract = "(Chemical Equation Presented) Halide or alkoxide free yttrium-salen complexes are excellent catalysts for the ring opening of epoxides mediated by TMSCN and TMSN3. Substrate to catalyst ratios up to 10000 have been realized in these potentially useful reactions, which can be run under solvent-free conditions. Even though the enantioselectivities for the TMSCN-mediated reaction remains modest (best 77{\%} ee), these studies with a highly tunable ligand system may provide further impetus for work in this important area of catalysis. Even though attempts to isolate a Y-cyanide complex, which was detected by in situ IR spectroscopy, failed, a related dimeric hydroxide complex was isolated. A kinetic study using in situ IR spectroscopy did not provide conclusive data to assign an order with respect to Y in this reaction.",
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Exceptionally active yttrium-salen complexes for the catalyzed ring opening of epoxides by TMSCN and TMSN3. / Saha, Biswajit; Lin, Mei Huey; RajanBabu, T. V.

In: Journal of Organic Chemistry, Vol. 72, No. 23, 09.11.2007, p. 8648-8655.

Research output: Contribution to journalArticle

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