Catalytic asymmetric oxidation of sulfides to sulfoxides using (R)-6,6 -Diphenyl-BINOL as a chiral ligand

Narotham V. Maddireddy, Himanshu M. Godbole, Girij P. Singh, Suvarna G. Kini, Gautham G. Shenoy

Research output: Contribution to journalArticle

Abstract

Abstract : The chiral metal complex produced in situ from (R)-6,6-Diphenyl-BINOL and Ti (O - i- Pr) 4 as a catalytic system for asymmetric sulfoxidation of aryl methyl and aryl benzyl sulfides in the presence of 70% aqueous TBHP as the oxidant has been investigated. The influence of variation of reagents mole ratios, temperature, solvent and oxidant was examined, and the optimized conditions were then used to oxidize a number of aryl methyl and aryl benzyl sulfides, producing sulfoxides in high enantiopurities (up to 90% ee) and good yields (up to 81%). Graphic Abstract: (R)-6,6’-Diphenyl Binol in combination with Ti(O-i-Pr) 4 has been developed as an efficient chiral ligand for the asymmetric oxidation of aryl methyl and aryl benzyl sulfides by using 70% aqueous TBHP as an oxidant. High enantioselectivity and good chemical yield have been achieved for various aryl methyl and aryl benzyl sulfides. [Figure not available: see fulltext.].

Original languageEnglish
Article number64
JournalJournal of Chemical Sciences
Volume131
Issue number7
DOIs
Publication statusPublished - 01-07-2019

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Sulfoxides
Sulfides
Oxidants
Ligands
Oxidation
Enantioselectivity
Coordination Complexes
benzyl sulfide
diphenyl
naphthol BINOL
Temperature

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Catalytic asymmetric oxidation of sulfides to sulfoxides using (R)-6,6 ′ -Diphenyl-BINOL as a chiral ligand",
abstract = "Abstract : The chiral metal complex produced in situ from (R)-6,6′-Diphenyl-BINOL and Ti (O - i- Pr) 4 as a catalytic system for asymmetric sulfoxidation of aryl methyl and aryl benzyl sulfides in the presence of 70{\%} aqueous TBHP as the oxidant has been investigated. The influence of variation of reagents mole ratios, temperature, solvent and oxidant was examined, and the optimized conditions were then used to oxidize a number of aryl methyl and aryl benzyl sulfides, producing sulfoxides in high enantiopurities (up to 90{\%} ee) and good yields (up to 81{\%}). Graphic Abstract: (R)-6,6’-Diphenyl Binol in combination with Ti(O-i-Pr) 4 has been developed as an efficient chiral ligand for the asymmetric oxidation of aryl methyl and aryl benzyl sulfides by using 70{\%} aqueous TBHP as an oxidant. High enantioselectivity and good chemical yield have been achieved for various aryl methyl and aryl benzyl sulfides. [Figure not available: see fulltext.].",
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Catalytic asymmetric oxidation of sulfides to sulfoxides using (R)-6,6 -Diphenyl-BINOL as a chiral ligand. / Maddireddy, Narotham V.; Godbole, Himanshu M.; Singh, Girij P.; Kini, Suvarna G.; Shenoy, Gautham G.

In: Journal of Chemical Sciences, Vol. 131, No. 7, 64, 01.07.2019.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Catalytic asymmetric oxidation of sulfides to sulfoxides using (R)-6,6 ′ -Diphenyl-BINOL as a chiral ligand

AU - Maddireddy, Narotham V.

AU - Godbole, Himanshu M.

AU - Singh, Girij P.

AU - Kini, Suvarna G.

AU - Shenoy, Gautham G.

PY - 2019/7/1

Y1 - 2019/7/1

N2 - Abstract : The chiral metal complex produced in situ from (R)-6,6′-Diphenyl-BINOL and Ti (O - i- Pr) 4 as a catalytic system for asymmetric sulfoxidation of aryl methyl and aryl benzyl sulfides in the presence of 70% aqueous TBHP as the oxidant has been investigated. The influence of variation of reagents mole ratios, temperature, solvent and oxidant was examined, and the optimized conditions were then used to oxidize a number of aryl methyl and aryl benzyl sulfides, producing sulfoxides in high enantiopurities (up to 90% ee) and good yields (up to 81%). Graphic Abstract: (R)-6,6’-Diphenyl Binol in combination with Ti(O-i-Pr) 4 has been developed as an efficient chiral ligand for the asymmetric oxidation of aryl methyl and aryl benzyl sulfides by using 70% aqueous TBHP as an oxidant. High enantioselectivity and good chemical yield have been achieved for various aryl methyl and aryl benzyl sulfides. [Figure not available: see fulltext.].

AB - Abstract : The chiral metal complex produced in situ from (R)-6,6′-Diphenyl-BINOL and Ti (O - i- Pr) 4 as a catalytic system for asymmetric sulfoxidation of aryl methyl and aryl benzyl sulfides in the presence of 70% aqueous TBHP as the oxidant has been investigated. The influence of variation of reagents mole ratios, temperature, solvent and oxidant was examined, and the optimized conditions were then used to oxidize a number of aryl methyl and aryl benzyl sulfides, producing sulfoxides in high enantiopurities (up to 90% ee) and good yields (up to 81%). Graphic Abstract: (R)-6,6’-Diphenyl Binol in combination with Ti(O-i-Pr) 4 has been developed as an efficient chiral ligand for the asymmetric oxidation of aryl methyl and aryl benzyl sulfides by using 70% aqueous TBHP as an oxidant. High enantioselectivity and good chemical yield have been achieved for various aryl methyl and aryl benzyl sulfides. [Figure not available: see fulltext.].

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