Carbon–Silicon Bond Formation in the Synthesis of Benzylic Silanes

Visco, Michael D.; Wieting, Joshua M.; Mattson, Anita E.

doi:10.1021/acs.orglett.6b01223

Cited by 22 publications

(21 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Efforts to identify a more efficient coupling reagent prompted us to investigate the reactivity of phenylsilane derivatives 4a-4e, synthesized according to known procedures (Figure 2). [15] Figure 2. Considered phenylsilane derivatives.…”

Section: Resultsmentioning

confidence: 99%

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

et al. 2020

View full text Add to dashboard Cite

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99%). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyltriacyloxysilane. From this mechanistic study, silicon tetracetate was shown as an efficient amine acylating agent.

show abstract

Section: Resultsmentioning

confidence: 99%

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Synthesis of other silanes: prepared according to the previously reported procedure (Visco et al, 2016), a 250 mL of three-necked flame-dried round-bottom flask was cooled at -20 o C under the atmosphere of nitrogen, charged with magnesium turnings (1.05 equiv. ), several iodine crystals and THF (10 mL).…”

Section: Synthesis Of Iminementioning

confidence: 99%

Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage

et al. 2020

View full text Add to dashboard Cite

An iron-catalyzed highly anti-Markovnikov selective, enantioselective hydrosilylation of vinylcyclopropanes with PhSiH 3 was reported for the preparation of valuable chiral allylic silanes via stereospecific C-C bond cleavage. Simultaneously, difficultly prepared chiral VCPs could be also obtained with moderate to excellent enantioselectivity via this kinetic resolution pathway. The chiral Zallylic silanes could be converted to various chiral allylic derivatives. A possible mechanism via an iron-silyl species was proposed based on experimental and computational studies.

show abstract

“…Organosilanols have important applications in various fields, 60 such as in polymetric materials science, organic synthesis, and medicinal chemistry. The chiral bis(silyl) alkane 2a could be completely oxidized to chiral silanols 4a 61 (Figures S12 and S122) or selectively oxidized to 5a 62 (Figures S70 and S121) in 76% or 81% yield, respectively (Scheme 4). The 2a could also undergo ruthenium-catalyzed hydrosilylation of alkyne to afford vinyl silane 6 (Figure S71) in 99% yield with a diastereomeric ratio (d.r.)…”

Section: Scheme 3 Gram-scale Reactionsmentioning

confidence: 99%

Cobalt-Catalyzed Asymmetric Synthesis of gem-Bis(silyl)alkanes by Double Hydrosilylation of Aliphatic Terminal Alkynes

Guo

Wang

Xing

et al. 2019

Chem

122

View full text Add to dashboard Cite

Chiral organosilanes are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. Compared with single-silyl compounds, bis(silyl) ones are understudied because of the lack of the efficient synthetic protocols. The development of efficient synthetic approaches to access bis(silyl) compounds is highly desirable for studying their basic properties and potential utilities. Here, a cobalt-catalyzed sequential double hydrosilylation of aliphatic alkynes was developed to synthesize highly enantioenriched gem-bis(silyl)alkanes. This protocol used simple aliphatic alkynes and silanes to construct valuable chiral gem-bis(silyl)alkanes. The control experiments, isotopic labeling experiments, kinetic studies, and density functional theory calculations were conducted to elucidate the reaction mechanism. The synthetic versatility of gem-bis(silyl)alkanes was demonstrated by the synthesis of chiral organosilanols, a-hydroxysilanes through selective C-Si bond transformation and hydrosilylation of alkynes to construct chiral silanes containing adjacent C-stereocenter and Si-stereocenter.

show abstract

Carbon–Silicon Bond Formation in the Synthesis of Benzylic Silanes

Cited by 22 publications

References 14 publications

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage

Cobalt-Catalyzed Asymmetric Synthesis of gem-Bis(silyl)alkanes by Double Hydrosilylation of Aliphatic Terminal Alkynes

Contact Info

Product

Resources

About