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Atom-efficient gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols: substrate scope and experimental and theoretical mechanistic investigation.

Biswas S, Dahlstrand C, Watile RA, Kalek M, Himo F, Samec JS - Chemistry (2013)

Bottom Line: Different gold sources and ligand effects were studied, and it was shown that gold(I) chloride gave the highest product yields.A sulfenylated allylic alcohol, generated by initial regioselective attack of the aryl thiol on the triple bond of the propargylic alcohol, was isolated, evaluated, and found to be an intermediate in the reaction.This in turn allows for a 1,2-hydride shift, generating the final product of the reaction.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, BMC, Uppsala University, Box 576, 75123, Uppsala (Sweden), Fax: (+46) 018-471-3818.

No MeSH data available.


Related in: MedlinePlus

Crossover experiment to investigate the intramolecularity of the hydride shift.
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sch08: Crossover experiment to investigate the intramolecularity of the hydride shift.


Atom-efficient gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols: substrate scope and experimental and theoretical mechanistic investigation.

Biswas S, Dahlstrand C, Watile RA, Kalek M, Himo F, Samec JS - Chemistry (2013)

Crossover experiment to investigate the intramolecularity of the hydride shift.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4524420&req=5

sch08: Crossover experiment to investigate the intramolecularity of the hydride shift.
Bottom Line: Different gold sources and ligand effects were studied, and it was shown that gold(I) chloride gave the highest product yields.A sulfenylated allylic alcohol, generated by initial regioselective attack of the aryl thiol on the triple bond of the propargylic alcohol, was isolated, evaluated, and found to be an intermediate in the reaction.This in turn allows for a 1,2-hydride shift, generating the final product of the reaction.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, BMC, Uppsala University, Box 576, 75123, Uppsala (Sweden), Fax: (+46) 018-471-3818.

No MeSH data available.


Related in: MedlinePlus