Chemoselective S-benzylation of indoline-2-thiones using benzyl alcohols

Jha, Mukund; Enaohwo, Oro; Marcellus, Ashley

doi:10.1016/j.tetlet.2009.10.050

Cited by 18 publications

(3 citation statements)

References 27 publications

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“…(F) Jha et al 1 described the first example of a chemoselective S-benzylation of indoline-2-thiones under mild conditions, using a variety of benzyl alcohols and BF 3 ·OEt 2 . In this procedure the aryl substituent has effects on the reactivity of benzyl alcohols toward S-benzylation and the results of those effects were also discussed.…”

Section: Scheme 1 Abstractsmentioning

confidence: 99%

“…Boron trifluoride etherate (BF 3 •OEt 2 , 1) is an effective reagent widely used for a variety of organic transformations, 1 especially for the construction of heterocycles systems by formation of carbon-carbon and carbon-heteroatom bond. Some applications in organic chemistry include the synthesis of quinolines 2 , spiro dihydroquinoline-oxindoles, 3 tetrahydrofurans, 4 trienes, 5 benzofurans 6 and dioxocanes.…”

Section: Introductionmentioning

confidence: 99%

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Boron Trifluoride Etherate

Muñoz

2012

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research spotlight Boron Trifluoride Etherate Compiled by July Andrea Hernández MuñozJuly Andrea Hernández Muñoz was born in Bucaramanga, Colombia in 1984. She graduated in Chemistry from the Universidad Industrial de Santander in 2009 and received her M.Sc. from the Universidade Federal do Rio de Janeiro in 2011. Currently, she is working towards her D.Sc. under the supervision of Professors Flavia Martins da Silva and Joel Jones Junior in organic chemistry. Her research interests focus on the development of novel synthetic methodologies for heterocyclic compounds with emphasis in green chemistry.

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Section: Scheme 1 Abstractsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Boron Trifluoride Etherate

Muñoz

2012

Synlett

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“…Recently we reported a palladium-catalyzed selective S-benzylation of unprotected mercaptobenzoic acids with benzylic alcohols using Pd(OAc) 2 /TPPMS (sodium diphenylphosphinobenzene-3sulfonate) catalysts in water. 4 Classical approaches for S-benzylation with benzyl alcohols, which are activated by Lewis acids such as boron trifluoride etherates, 5 yttrium triflates, 6 ZnI 2 , 7 and ZrCl 4 , 8 have been reported.…”

Section: Introductionmentioning

confidence: 99%

Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via (η³-benzyl)palladium(ii) cations in water

Hikawa

Azumaya

2014

Org. Biomol. Chem.

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Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the (η(3)-benzyl)palladium(II) cation in water. Notably, these palladium(0) complexes could play an important role in formation of active (η(3)-benzyl)palladium(II) cation complexes followed by S-benzylation. Hammett studies on the rate constants of S-benzylation by various substituted alcohols show good correlation between log(kX/kH) and the σ(+) value of the respective substituents. From the slope, negative ρ values are obtained, suggesting that there is a build-up of positive charge in the transition state. Water plays an important role in the catalytic system for sp(3) C-O bond activation and stabilization of the activated Pd(II) cation species. The catalytic system can be performed using only 2.5 mol% Pd2(dba)3 without the phosphine ligand or other additives.

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