58144-45-9

Upstream product

• 608-33-3 2,6-dibromophenol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 58144-39-1 {3-bromo-2-[(trimethylsilyl)oxy]phenyl}trimethylsilane 
• 58144-49-3 2-bromo-6-(trimethylsilyl)phenol 
• 18036-71-0 2,6-bis(trimethylsilyl)phenol 
• 1092542-31-8 2-bromo-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 97391-18-9 2,6-bis(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors

Stable 2-(trimethylsilyl)phenyl trimethylsilyl ethers, readily obtained from the corresponding halogenated phenols in two steps, were identified as novel benzyne precursors. These species were converted to benzynes by a domino reaction of O-desilylation,

Mild synthesis of triarylsulfonium salts with arynes

Reactions between arynes and alkyl sulfides have been extensively studied over the past few decades. These reactions commonly end with a dealkylation process and thus deliver thioethers as final products. In contrast, the transformation described furnishes valuable triarylsulfonium salts, in lieu of thioethers, from arynes and diarylsulfides. The reaction features mild conditions and a broad substrate scope. A suite of functional groups such as ketones, esters, nitriles, aryl ethers and aryl halides is tolerated, which can be issues faced by traditional synthetic methods. The practicality of the reaction and its extension to the synthesis of triphenyl selenonium salt are also exhibited herein.

Continuous-flow synthesis of trimethylsilylphenyl perfluorosulfonate benzyne precursors

2-(Trimethylsilyl)phenyl perfluorosulfonated aryne precursors may now be accessed using flow chemistry, enabling the fast preparation of pure compounds with no requirement for low temperature lithiation or column chromatography. The process has been adapted to novel nonaflate precursors, utilizing the cheaper and more user-friendly nonaflyl fluoride reagent. The resultant nonaflates are shown to successfully participate in a range of aryne reaction classes.

Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives

Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti

Ortho-Selective nucleophilic addition of amines to 3-borylbenzynes: Synthesis of multisubstituted anilines by the triple role of the boryl group

Nucleophilic addition of amines to 3-[(dan)boryl]benzynes (dan = 1,8-diaminonaphthalene) generated by a fluoride ion proceeded with high ortho-selectivity to give 2-borylaniline derivatives, under conditions that are tolerant to various functional groups. The (dan)boryl group of the adduct was hydrolyzed into a boronic acid under acidic conditions, which could further serve for various C-C, C-O, C-N, and C-H bond-formation reactions. The overall process provides a promising entry for preparing multisubstituted aniline derivatives.

Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes

We report an experimental and computational study of 3-silylarynes. The addition of nucleophiles yield ortho-substituted products as a result of aryne distortion, but meta-substituted products form predominately when the nucleophile is large. Computations correctly predict the preferred site of attack observed in both nucleophilic addition and cycloaddition experiments. Nucleophilic additions to 3-tert-butylbenzyne, which is not significantly distorted, give meta-substituted products.