Samarium (II) diiodide‐induced reductive cleavage of SeSe and TeTe bond in diphenyl diselenide and ditelluride leading to a samarium phenylselenolate and tellurolate: Preparation of unsymmetrical alkylphenyl selenides and tellurides

Fukuzawa, Shin‐ichi; Niimoto, Yasuhiko; Fujinami, Tatsuo; Sakai, Shizuyoshi

doi:10.1002/hc.520010611

Cited by 37 publications

(5 citation statements)

References 23 publications

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“…In the course of studying reactions mediated by SmI 2 , we and others have noticed the negative impact of the quality of some batches of samarium metal on the efficiency of SmI 2 formation . In the worst cases, it has been noted that the preparation of SmI 2 using a batch of samarium metal might fail completely under standard conditions.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Samarium(II) Iodide: Quantitative Evaluation of the Effect of Water, Oxygen, and Peroxide Content, Preparative Methods, and the Activation of Samarium Metal

2012

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Samarium(II) iodide (SmI(2)) is one of the most important reducing agents in organic synthesis. Synthetic chemistry promoted by SmI(2) depends on the efficient and reliable preparation of the reagent. Unfortunately, users can experience difficulties preparing the reagent, and this has prevented realization of the full synthetic potential of SmI(2). To provide synthetic chemists with general and reliable methods for the preparation of SmI(2), a systematic evaluation of the factors involved in its synthesis has been carried out. Our studies confirm that SmI(2) is a user-friendly reagent. Factors such as water, oxygen, and peroxide content in THF have little influence on the synthesis of SmI(2). In addition, the use of specialized glovebox equipment or Schlenk techniques is not required for the preparation of SmI(2). However, our studies suggest that the quality of samarium metal is an important factor and that the use of low quality metal is the main cause of failed preparations of the reagent. Accordingly, we report a straightforward method for activation of "inactive" samarium metal and demonstrate the broad utility of this protocol through the electron transfer reductions of a range of substrates using SmI(2) prepared from otherwise "inactive" metal. An investigation into the stability of SmI(2) solutions and an evaluation of commercially available solutions of the reagent is also reported.

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Section: Resultsmentioning

confidence: 99%

Preparation of Samarium(II) Iodide: Quantitative Evaluation of the Effect of Water, Oxygen, and Peroxide Content, Preparative Methods, and the Activation of Samarium Metal

2012

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“…The above appearance showed that nitro groups and Se Se bonds were simultaneously reduced by SmI 2 . According to the literature [5,6], we considered that an intermediate 2 could be generated in situ during the reduction procedure. Then, many kinds of electrophilic reagents were tested to react with these species 2.…”

Section: Resultsmentioning

confidence: 99%

Conversion of bis(o‐nitrophenyl)diselenides to heterocycles containing selenium and nitrogen with the aid of samarium diiodide

Chen

Zhong

Zhang

2002

Heteroatom Chemistry

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Treatment of bis(o-nitrophenyl)diselenides with SmI 2 led to simultaneous reduction of nitro groups and reductive cleavage of Se Se bonds as well as to the formation of the intermediates 2.The intermediates 2 were "living" double-anions formed in situ, and reacted readily with ω-bromoketones and α-bromocarboxylic acid derivatives to afford the desired 2H-1,4-benzoselenazines and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields and under mild conditions.

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“…1. 20 We are grateful to the National Natural Science Foundation of China and Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, for ®nancial support.…”

Section: Methodsmentioning

confidence: 99%

Reductive Cleavage of the Se–Si Bond in Arylselenotrimethylsilanes: Novel Method for the Synthesis of Unsymmetrical Selenides†

Zhang¹,

Zhang²

1998

J. Chem. Res.

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Samarium (II) diiodide‐induced reductive cleavage of SeSe and TeTe bond in diphenyl diselenide and ditelluride leading to a samarium phenylselenolate and tellurolate: Preparation of unsymmetrical alkylphenyl selenides and tellurides

Abstract: Diphenyl diselenide and diphenyl ditelluride were reduced by samarium (11)

Cited by 37 publications

References 23 publications

Preparation of Samarium(II) Iodide: Quantitative Evaluation of the Effect of Water, Oxygen, and Peroxide Content, Preparative Methods, and the Activation of Samarium Metal

Preparation of Samarium(II) Iodide: Quantitative Evaluation of the Effect of Water, Oxygen, and Peroxide Content, Preparative Methods, and the Activation of Samarium Metal

Conversion of bis(o‐nitrophenyl)diselenides to heterocycles containing selenium and nitrogen with the aid of samarium diiodide

Reductive Cleavage of the Se–Si Bond in Arylselenotrimethylsilanes: Novel Method for the Synthesis of Unsymmetrical Selenides†

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