65943-03-5Relevant academic research and scientific papers
Borylative Heterocyclization without Air-Free Techniques
Blum, Suzanne A.,Gao, Chao,Nakao, Shuichi
, p. 10350 - 10368 (2020/09/23)
In contrast to previously reported borylative heterocyclization methods, a reaction here proceeds without air-free techniques to access synthetically useful borylated thiophenes, benzothiophenes, and isocoumarins. A comparison of stability/decomposition rates in air of several catecholboronic ester (Bcat) compounds derived from different heterocycle cores showed a strong dependence on the heterocycle structure. Lessons learned from this comparison were then harnessed for the development of borylative heterocyclization reactions under ambient-atmosphere conditions and with wet solvent. In contrast to literature reports suggesting general moisture sensitivity, a subset of Bcat products resulting from this technique were chromatography-stable and directly isolable, obviating the requirement for an extra synthetic transformation into more stable boron species, such as pinacolboronic esters (Bpin), for isolation. The isolated Bcat products were amenable to various downstream functionalization reactions, including reactions that were not accessible with their better-known Bpin counterparts, showing the complementarity of Bcat reaction partners and expanding their known chemistry. These results suggest the value of conceptual revisitation of substitution and solvent influence on stability and isolability of organo-Bcat compound classes and lay the groundwork for development of additional practical borylative methods in air.
Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration
Bel Abed, Hassen,Blum, Suzanne A.
, p. 6673 - 6677 (2018/10/24)
A simple, regiocontrolled, and transition-metal-free approach to access exclusively 3-borylated thiophene derivatives is reported. The commercially available B-chlorocatecholborane reagent (ClBcat) acts as a carbophilic Lewis acid to activate the alkyne i
Vinyl thioether compound and preparation method thereof
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Paragraph 0017; 0020, (2017/08/28)
The invention relates to a vinyl thioether compound. The structural formula of the compound is as shown in the specification, R1 or R2 is selected from heteroaryl or aryl, the R1 and the R2 are the same or different, the aryl is phenyl or naphthyl, the vinyl thioether compound is prepared by taking 1, 3-diacetylene compounds and sulfoxide as raw materials in organic solvents, controlling reaction temperature at 120-130 DEG C, performing reaction for 12-48 hours and then performing extraction and separation. Compared with the prior art, the vinyl thioether compound has the advantages that the sulfoxide serves as a sulfur source, the compound is applicable to different types of 1, 3-diacetylene compounds, simple and convenient to operate and high in yield, reaction conditions are mild, and the prepared vinyl thioether compound can be used as an organic photoelectric material, a medical intermediate or an organic synthesis intermediate.
Green synthesis of halogenated thiophenes, selenophenes and benzo[b]selenophenes using sodium halides as a source of electrophilic halogens
Kesharwani, Tanay,Giraudy, Krystal A.,Morgan, Jordan L.,Kornman, Cory,Olaitan, Abayomi D.
supporting information, p. 638 - 641 (2017/01/25)
Herein, we report the first synthesis of chlorinated benzo[b]selenophenes via environmentally friendly electrophilic chlorocyclization reaction using “table salt” as a source of “electrophilic chlorine” and ethanol as a solvent. In addition, the synthesis
