Silanes as reducing agents

Colvin, Ernest W.

doi:10.1016/b978-0-408-10831-7.50027-5

Cited by 9 publications

(1 citation statement)

References 65 publications

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“…Organosilicon compounds are widely utilized as an important building unit in synthetic, medicinal, polymer, and materials chemistry . Hydrosilylation is one of the most straightforward methods to introduce the silyl group into organic molecules by reacting with unsaturated bonds. − More recently, dehydrogenative silylation of unactivated C–H bonds has also drawn special attention as an alternative strategy to provide silylated alkanes and arenes .…”

Section: Introductionmentioning

confidence: 99%

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds

2015

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Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp(3) C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylation as an initial step depending on the substituent position, followed by selective hydrosilylation of enamine double bonds eventually affording β-silylated azacyclic compounds.

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Section: Introductionmentioning

confidence: 99%

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds

2015

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Transition‐Metal‐Free C−H Silylation: An Emerging Strategy

et al. 2021

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Silicon‐containing molecules are of great interest with widespread applications in several research areas such as polymer chemistry, materials science, medicinal chemistry, and complex molecule synthesis. Transition‐metal‐free C−H silylation is an essential process because this process is useful in fabricating carbon‐silicon bonds which can be further transformed into a number of other compounds. Since transition‐metal‐catalyzed C−H bond silylation is a developed field, therefore this context only contains transition‐metal‐free pathways for transforming C−H bond to C−Si (Si=SiR3) bond. This review has been further categorized and subcategorized based on intermediates involved and catalysts used during this transformation. This synopsis summarizes recent developments in the area of silicon chemistry with a focus of innovative transition‐metal‐free catalytic silylation using different strategies such as free radical, base promoted, Brønsted acid, Lewis acid, and frustrated Lewis pair.

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Chemoselective Silylative Reduction of Conjugated Nitriles under Metal‐Free Catalytic Conditions: β‐Silyl Amines and Enamines

et al. 2015

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The B(C 6 F 5 ) 3 -catalyzed silylative reduction of conjugated nitriles has been developed to affords ynthetically valuable b-silyl amines.T he reaction is chemoselective and proceeds under mild conditions.M echanistic elucidation indicates that it proceeds by rapid double hydrosilylation of the conjugated nitrile to an enamine intermediate which is subsequently reduced to the b-silyl amine,thus forming anew C(sp 3 )ÀSi bond. Based on this mechanistic understanding, ap reparative route to enamines was also established using bulky silanes.

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Silanes as reducing agents

Cited by 9 publications

References 65 publications

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds

Transition‐Metal‐Free C−H Silylation: An Emerging Strategy

Chemoselective Silylative Reduction of Conjugated Nitriles under Metal‐Free Catalytic Conditions: β‐Silyl Amines and Enamines

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Silanes as reducing agents

Cited by 9 publications

References 65 publications

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C–Si Bonds

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C–Si Bonds

Transition‐Metal‐Free C−H Silylation: An Emerging Strategy

Chemoselective Silylative Reduction of Conjugated Nitriles under Metal‐Free Catalytic Conditions: β‐Silyl Amines and Enamines

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Product

Resources

About

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp³ C–Si Bonds