Dehydrogenative sulfenylation of cyclohexanones

Trost, Barry M.; Rigby, James H.

doi:10.1016/s0040-4039(01)94635-0

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Reactions Of Diphenyl Disulfide With Carbon Nucleophiles1

Introduction1

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2017

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Cited by 16 publications

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“…Lactone 4 enolates also react with PhSSPh, leading ( Cyclohexanones undergo dehydrogenative sulfenylation upon reaction with PhSSPh in methanolic NaOMe to give o-phenylthio phenols (eq 7). 9 This reaction is interesting, in that the PhSSPh appears to behave both as a source of electrophilic phenylthio functionality and as an oxidizing agent in the course of the transformation. PhSSPh (7) O SPh OH NaOMe 42%…”

Section: Reactions Of Diphenyl Disulfide With Carbon Nucleophilesmentioning

confidence: 99%

Diphenyl Disulfide

Byers¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Section: Reactions Of Diphenyl Disulfide With Carbon Nucleophilesmentioning

confidence: 99%

Diphenyl Disulfide

Byers¹

2001

Encyclopedia of Reagents for Organic Synthesis

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“…[12c] Thus, this area needs to be further explored. Trost and Rigby reported the treatment of disulfides with strong bases under aprotic conditions with cyclic ketones. Compounds with a small number of carbon atoms underwent fragmentation instead of sulfenylation, and sometimes aromatization, though compound with a larger number of carbon atoms resisted fragmentation and gave mono‐ and disubstituted products in a 1:1 ratio.…”

Section: Introductionmentioning

confidence: 99%

Towards the Iodine‐Catalyzed Regioselective Sulfenylation of Unsymmetrical Ketones

et al. 2017

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An efficient method for the synthesis of β‐keto sulfides was developed. A thermodynamically stable enolate was generated from unsymmetrical ketones and was found to react with sulfenyl iodides generated in situ from various disulfides to give α‐sulfenylation products. Potassium tert‐butoxide was used in a solvent mixture of tBuOH/1,3‐dimethyl‐2‐imidazolidinone (DMI, 7:3) at a mild reaction temperature of 40 °C. This iodine‐catalyzed method led to products in excellent yields up to 92 % within 2 h. The method is economical and no hazardous waste products are recovered throughout the process. The protocol is important, as unmodified ketones (linear and cyclic) are easily sulfenylated, which is otherwise not trivial. The Lewis acid FeCl3 could be used as an alternative reagent to avoid the use of base and DMI. However, treatment with this Lewis acid lowered the yields and the maximum yield obtained was 85 %.

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