Ring opening reactions of thiiranes by alkoxo- and aryloxo-gold(I) complexes

Usui, Yoko; Noma, Junko; Hirano, Masafumi; Komiya, Sanshiro

doi:10.1039/a907574g

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…207 The research group of Komiya published a study describing the alkoxymetalation of thiiranes with gold complexes 433 (Scheme 146). 208 Monosubstituted thiiranes 310 gave mixtures of regioisomeric products 436 and 437. Whereas cisdisubstituted thiiranes 434 yielded a single diastereomeric product 438, the trans-isomer 435 afforded a mixture of diastereomers 438 and 439.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

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The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

2014

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

“…The research group of Komiya published a study describing the alkoxymetalation of thiiranes with gold complexes 433 (Scheme ) . Monosubstituted thiiranes 310 gave mixtures of regioisomeric products 436 and 437 .…”

Section: Thiiranesmentioning

confidence: 99%

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

2014

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“…In contrast, analogous non‐fluorinated alkoxido gold complexes are more thoroughly investigated [56] and have been used as a catalyst for Knöevenagel condensation reactions [57] . They can abstract hydrides from metal hydrides yielding gold metal complexes [58] or protons from several organic compounds, [59] as well as cleave C−S [60] and C−Si [61] bonds.…”

Section: Introductionmentioning

confidence: 99%

Reactivity of [AuF₃(SIMes)]: Pathway to Unprecedented Structural Motifs

Winter

Ellwanger

Limberg

et al. 2023

Chemistry A European J

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We report on a comprehensive reactivity study starting from [AuF3(SIMes)] to synthesize different motifs of monomeric gold(III) fluorides. A plethora of different ligands has been introduced in a mono‐substitution yielding trans‐[AuF2X(SIMes)] including alkynido, cyanido, azido, and a set of perfluoroalkoxido complexes. The latter were better accomplished via use of perfluorinated carbonyl‐bearing molecules, which is unprecedented in gold chemistry. In case of the cyanide and azide, triple substitution gave rise to the corresponding [AuX3(SIMes)] complexes. Comparison of the chemical shift of the carbene carbon atom in the 13C{1H} NMR spectrum, the calculated SIMes affinity and the Au−C bond length in the solid state with related literature‐known complexes yields a classification of trans‐influences for a variety of ligands attached to the gold center. Therein, the mixed fluorido perfluoroalkoxido complexes have a similar SIMes affinity to AuF3 with a very low Gibbs energy of formation when using the perfluoro carbonyl route.

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Thiosilanes in sulfur chemistry: A general approach to silyl thiaheterocycles and their use in stereoselective synthesis

Capperucci¹,

Degl’Innocenti²,

Pollicino³

et al. 2007

Heteroatom Chemistry

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Abstract2‐Silyl five‐membered sulfurated heterocycles can be efficiently accessed through reaction of bromo(methoxy)methyl trimethylsilane with suitable β‐substituted mercaptans HS‐CH2CH2‐XH, leading to the formation of 2‐silyl‐1,3‐dithiols, 2‐silyl‐1,3‐thiazolidines, and 2‐silyl‐1,3‐oxathiolanes. β‐Mercaptoalcohols are obtained through regioselective ring opening of epoxides with bis(trimethylsilyl)sulfide (HMDST). In a similar way, thiiranes and aziridines react with HMDST, leading to the formation of 1,2‐dithiols and β‐aminothiols. Fluoride ion induced functionalization of the pentaatomic heterocycles smoothly affords the transfer of the heterocyclic ring on electrophiles, thus showing these silyl derivatives as a new class of acyl anion equivalents. When stereodefined compounds are reacted, the stereoinformation is transferred from the carbon–silicon to the newly formed carbon–carbon bond. © 2007 Wiley Periodicals, Inc. 18:516–526, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20345

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Ring opening reactions of thiiranes by alkoxo- and aryloxo-gold(I) complexes

Cited by 9 publications

References 21 publications

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

Reactivity of [AuF₃(SIMes)]: Pathway to Unprecedented Structural Motifs

Thiosilanes in sulfur chemistry: A general approach to silyl thiaheterocycles and their use in stereoselective synthesis

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Ring opening reactions of thiiranes by alkoxo- and aryloxo-gold(I) complexes

Cited by 9 publications

References 21 publications

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

Reactivity of [AuF3(SIMes)]: Pathway to Unprecedented Structural Motifs

Thiosilanes in sulfur chemistry: A general approach to silyl thiaheterocycles and their use in stereoselective synthesis

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Product

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Reactivity of [AuF₃(SIMes)]: Pathway to Unprecedented Structural Motifs