Electrochemical Hydrosilylation of Alkynes

Biremond, Tony; Jubault, Philippe; Poisson, Thomas

doi:10.1021/acsorginorgau.1c00035

Cited by 21 publications

(12 citation statements)

References 30 publications

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“…Recent studies show a possible hydrosilylation of alkynes via the electrochemical reaction pathway. [167] However, the oxidation of SiÀ B bonds is beyond the scope of our review and has been already discussed elsewhere. [35] Recent studies by He and co-workers, [69] have shown that the use of a HAT mediator generates a silyl radical that can be scavenged by unsaturated hydrocarbons.…”

Section: Si-c Bond Formationmentioning

confidence: 99%

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: Si-c Bond Formationmentioning

confidence: 99%

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

2023

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“…[84][85][86][87][88] Another solution is to use Si-B reagents, which could generate silyl radicals by direct anodic oxidation in the presence of a base (Scheme 21, right, path 2). 89 On the basis of the two strategies, several reports have emerged in recent years to exploit the application of silyl radical intermediates, which expand the potential value of this methodology.…”

Section: Electro-enabled Radical Silylationmentioning

confidence: 99%

“…In 2022, Poisson and co-workers reported an electrochemical hydrosilylation of alkynes without the assistance of NHPI (Scheme 31). 89 In this process, the Suginome reagent (PhMe 2 Si-Bpin) was used to enable the formation of a silyl radical. A large panel of aryl alkynes and alkyl-substituted alkynes could deliver the desired products in good yields with high selectivities in favor of the linear products.…”

Section: Electro-generated Silyl Radicals By Anodic Oxidationmentioning

confidence: 99%

Recent advances in photo- and electro-enabled radical silylation

Ren

et al. 2022

Org. Chem. Front.

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“…In sharp contrast, synthesis of geminal or vicinal borosilanes via radical approaches is rarely explored 19 – 21 . Even though hydrosilylation of alkenes through hydrogen atom transfer catalysis or single electron transfer catalysis have been developed 19 , 22 – 28 and many alkenyl boronates are commercially available, regiocontrol in radical hydrosilylation of substituted alkenyl boronates remains challenging (Fig. 1A ).…”

Section: Introductionmentioning

confidence: 99%

Photocatalyzed regioselective hydrosilylation for the divergent synthesis of geminal and vicinal borosilanes

Kong

Zhang

et al. 2023

Nat Commun

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Geminal and vicinal borosilanes are useful building blocks in synthetic chemistry and material science. Hydrosilylation/hydroborylation of unsaturated systems offer expedient access to these motifs. In contrast to the well-established transition-metal-catalyzed methods, radical approaches are rarely explored. Herein we report the synthesis of geminal borosilanes from α-selective hydrosilylation of alkenyl boronates via photoinduced hydrogen atom transfer (HAT) catalysis. Mechanistic studies implicate that the α-selectivity originates from a kinetically favored radical addition and an energetically favored HAT process. We further demonstrate selective synthesis of vicinal borosilanes through hydrosilylation of allyl boronates via 1,2-boron radical migration. These strategies exhibit broad scopes across primary, secondary, and tertiary silanes and various boron compounds. The synthetic utility is evidenced by access to multi-borosilanes in a diverse fashion and scaling up by continuous-flow synthesis.

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Electrochemical Hydrosilylation of Alkynes

Cited by 21 publications

References 30 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

Photocatalyzed regioselective hydrosilylation for the divergent synthesis of geminal and vicinal borosilanes

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