Electrochemical reduction of alkoxychlorosilanes for Si–Si bond formation

Ohshita, Joji; Hino, Koichi; Iwawaki, Tomonori; Kunai, Atsutaka

doi:10.1016/j.jelechem.2008.10.022

Cited by 7 publications

(9 citation statements)

References 13 publications

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“… Possible interactions of supporting electrolyte with halosilanes: a) halogen exchange at chlorosilane, [47,58–62] b) equilibration reaction of hydrochlorosilanes via tetraalkylammonium cations [64–67] …”

Section: Useful Information For Electrochemical Silane Synthesismentioning

confidence: 99%

“…[79][80][81] Otherwise, the metal chloride precipitates off the mixture depending on their solubility (Scheme 3, c II). According to suitable oxidation potentials (Table 1), Mg, [56][57][58]67,73,[83][84][85][86][87][88][89] Al, [80,82,85,90,91] Zn, [82,92] Ni, [85] Cu,, [59,85,[93][94][95] Ag, [79] and Hg [81,96,97] could be used as sacrificial anode materials.…”

Section: Sacrificial Anode Materialsmentioning

confidence: 99%

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General Concepts and Recent Advances in the Electrochemical Transformation of Chloro‐ and Hydrosilanes

2023

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Organosilanes play an important role in organic synthesis as well as in a variety of further areas, ranging from life science to transportation. Especially, the electrochemical access has become increasingly important in the past years and developed into an essential topic due to new conceptual approaches and mediated reaction control. With the commercial availability of high‐quality electrochemical equipment, the technical requirements for electro‐conversion are at hand to a wide audience. This results in the need for a concise survey of electrochemical silane transformation, appropriate for novices as well as experts alike. This review provides an overview of the most relevant work in this field, identifies common obstacles in working with chlorosilanes and hydrosilanes and bridges the gap between known techniques and novel methods with respect to their electrochemical conversion. The historical development is outlined with reference to the various cathodic as well as anodic conversions and should encourage to expand the research field of electrochemical silane transformation.

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Section: Useful Information For Electrochemical Silane Synthesismentioning

confidence: 99%

Section: Sacrificial Anode Materialsmentioning

confidence: 99%

General Concepts and Recent Advances in the Electrochemical Transformation of Chloro‐ and Hydrosilanes

2023

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“…The early studies about organosilicon electrochemistry mainly concentrated on cathodic reduction, which can be divided into two types: (1) cathodic cleavage of chlorosilanes to produce silyl radicals (Scheme 21, left), which could further generate silyl anions to react with other electrophiles; 80,81 (2) cathodic generation of carbanions or other nucleophiles, 82 which could undergo S N 2 attack on chlorosilanes to form a Si–C bond. 83 The latter does not involve silyl radicals, so it is out of the scope of this review.…”

Section: Electro-enabled Radical Silylationmentioning

confidence: 99%

“…21,[65][66][67] In recent years, with the rapid iteration of organic electrochemistry, [68][69][70][71][72][73][74][75][76][77][78][79] organosilicon electrochemistry has emerged as a powerful and efficient synthetic approach for accessing organosilicon compounds in a sustainable manner, which continues to give impetus for the innovation of organosilicon chemistry. The early studies about organosilicon electrochemistry mainly concentrated on cathodic reduction, which can be divided into two types: (1) cathodic cleavage of chlorosilanes to produce silyl radicals (Scheme 21, left), which could further generate silyl anions to react with other electrophiles; 80,81 (2) cathodic generation of carbanions or other nucleophiles, 82 which could undergo S N 2 attack on chlorosilanes to form a Si-C bond. 83 The latter does not involve silyl radicals, so it is out of the scope of this review.…”

Section: Electro-enabled Radical Silylationmentioning

confidence: 99%

Recent advances in photo- and electro-enabled radical silylation

Ren

et al. 2022

Org. Chem. Front.

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“…Starting in the late 1970s, Hengge and coworkers published two reports on the electroreduction of chlorosilanes to afford disilanes in good Faradaic yield 30,31 , although their approach utilizes a sacrificial Hg, Pb, or Cd anode, generating highly toxic metal salts as byproducts. In separate advances, Shono 32,33 , Kunai 34,35 , and Grogger 36 developed this system further to employ less hazardous electrode materials and expand the reaction scope to asymmetric disilane and trisilane formations 33,34 . However, all these approaches require a large excess of one coupling partner-two or more equivalentsto ensure satisfactory cross-coupling selectivity.…”

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confidence: 99%

Electrochemical logic to synthesize disilanes and oligosilanes from chlorosilanes

guan

Jiang

et al. 2023

Preprint

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Oligosilanes are important compounds in industrial and synthetic chemistry. Here, we develop a general approach for the synthesis of linear and cyclic oligosilanes via the reductive activation of readily available chlorosilanes. The efficient and selective generation of silyl anion intermediates, which are arduous to achieve by other means, allows for the synthesis of various novel oligosilanes. In particular, this work presents a modular synthesis for a variety of functionalized cyclosilanes, which may give rise to materials with distinct properties from linear silanes but remain challenging synthetic targets. In comparison to the traditional Wurtz coupling, our method features milder conditions and improved chemoselectivity, broadening the functional groups that are compatible in oligosilane preparation. Computational studies support a mechanism whereby differential activation of two sterically and electronically distinct chlorosilanes are achieved in an electrochemically driven radical-polar crossover mechanism.

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Electrochemical reduction of alkoxychlorosilanes for Si–Si bond formation

Cited by 7 publications

References 13 publications

General Concepts and Recent Advances in the Electrochemical Transformation of Chloro‐ and Hydrosilanes

General Concepts and Recent Advances in the Electrochemical Transformation of Chloro‐ and Hydrosilanes

Recent advances in photo- and electro-enabled radical silylation

Electrochemical logic to synthesize disilanes and oligosilanes from chlorosilanes

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