Photoelectron spectroscopic investigation of phenyl isocyanato silanes

Pasinszki, Tibor; Réffy, József; Veszprémi, Tamás

doi:10.1007/bf00810924

“…Silyl isocyanates have been utilized as silane coupling and surface finishing agents, [12] and are potentially useful as carbamoyl synthons for organic synthesis. [12,13] Up to the present, the vast majority of silyl isocyanates have been synthesized using chlorosilanes and metal cyanates (e.g., silver cyanate) [Eq.…”

mentioning

confidence: 99%

Heterogeneous‐Gold‐Catalyzed Acceptorless Cross‐Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea

Taniguchi

¹

,

Itagaki

²

,

Yamaguchi

³

et al. 2013

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Cross-coupling reactions (e.g., Suzuki, Negishi, Heck, Stille, Kumada, and Buchwald-Hartwig reactions) are of paramount importance and have proven useful for the design of molecules. [1] Although cross-coupling reactions can precisely construct new C À C, C À X, and X À X bonds (X = heteroatom), they usually utilize preactivated substrates (e.g., halides, tosylates, and triflates) and require transmetalation steps, which concurrently generate at least stoichiometric amounts of metal salts as waste. [1] Recently, cross-dehydrogenative coupling reactions by direct activation of CÀH or XÀH bonds have been emerging as synthetic tools because they are more atom efficient and environmentally benign than classical cross-coupling reactions. [2] To date, several efficient crossdehydrogenative coupling reactions using hydrogen acceptors (oxidants) such as tert-butyl hydroperoxide, [3] hydrogen peroxide, [4] and molecular oxygen [5] have been developed. Acceptorless cross-dehydrogenative coupling reactions have also been developed. [6] Quite recently, we have also reported C À N (terminal alkynes and amides), [7] P À N (H-phosphonates and amides), [8] SiÀN (hydrosilanes and indoles), [9] and SiÀC (hydrosilanes and terminal alkynes) [10] bond-forming reactions by cross-dehydrogenative coupling strategy. Herein, we successfully developed a novel green synthetic route to silyl isocyanates through heterogeneous-gold-catalyzed, acceptorless cross-dehydrogenative coupling of hydrosilanes and isocyanic acid (generated by in situ thermolysis of urea [11] ) [Eq. (1)].

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“…Silyl isocyanates have been utilized as silane coupling and surface finishing agents, [12] and are potentially useful as carbamoyl synthons for organic synthesis. [12,13] Up to the present, the vast majority of silyl isocyanates have been synthesized using chlorosilanes and metal cyanates (e.g., silver cyanate) [Eq. (2)].…”

mentioning

confidence: 99%

Heterogeneous‐Gold‐Catalyzed Acceptorless Cross‐Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea

Taniguchi

¹

,

Itagaki

²

,

Yamaguchi

³

et al. 2013

View full text Add to dashboard Cite

Cross-coupling reactions (e.g., Suzuki, Negishi, Heck, Stille, Kumada, and Buchwald-Hartwig reactions) are of paramount importance and have proven useful for the design of molecules. [1] Although cross-coupling reactions can precisely construct new C À C, C À X, and X À X bonds (X = heteroatom), they usually utilize preactivated substrates (e.g., halides, tosylates, and triflates) and require transmetalation steps, which concurrently generate at least stoichiometric amounts of metal salts as waste. [1] Recently, cross-dehydrogenative coupling reactions by direct activation of CÀH or XÀH bonds have been emerging as synthetic tools because they are more atom efficient and environmentally benign than classical cross-coupling reactions. [2] To date, several efficient crossdehydrogenative coupling reactions using hydrogen acceptors (oxidants) such as tert-butyl hydroperoxide, [3] hydrogen peroxide, [4] and molecular oxygen [5] have been developed. Acceptorless cross-dehydrogenative coupling reactions have also been developed. [6] Quite recently, we have also reported C À N (terminal alkynes and amides), [7] P À N (H-phosphonates and amides), [8] SiÀN (hydrosilanes and indoles), [9] and SiÀC (hydrosilanes and terminal alkynes) [10] bond-forming reactions by cross-dehydrogenative coupling strategy. Herein, we successfully developed a novel green synthetic route to silyl isocyanates through heterogeneous-gold-catalyzed, acceptorless cross-dehydrogenative coupling of hydrosilanes and isocyanic acid (generated by in situ thermolysis of urea [11] ) [Eq. (1)].

show abstract

(HeliumI)‐Photoelectron Spectra of Silicon Compounds: History and Achievements Concerning their Molecular States

Bock

¹

,

Solouki

²

2009

Patai's Chemistry of Functional Groups

0

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Photoelectron spectroscopic investigation of phenyl isocyanato silanes

Cited by 6 publications

References 19 publications

Heterogeneous‐Gold‐Catalyzed Acceptorless Cross‐Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea

Heterogeneous‐Gold‐Catalyzed Acceptorless Cross‐Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea

Heterogeneous‐Gold‐Catalyzed Acceptorless Cross‐Dehydrogenative Coupling of Hydrosilanes and Isocyanic Acid Generated in situ from Urea

(HeliumI)‐Photoelectron Spectra of Silicon Compounds: History and Achievements Concerning their Molecular States

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