97391-18-9

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 58144-39-1 {3-bromo-2-[(trimethylsilyl)oxy]phenyl}trimethylsilane 
• 72525-60-1 hexamethyldisilazan 
• 58144-49-3 2-bromo-6-(trimethylsilyl)phenol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 608-33-3 2,6-dibromophenol 
• 18036-71-0 2,6-bis(trimethylsilyl)phenol 
• 58144-45-9 2,6-dibromophenol O-trimethylsilyl ether 

Downstream Products

• 97391-21-4 2-(2,2,2-Trifluoro-ethoxy)-1,3-bis-trimethylsilanyl-benzene 
• 97391-26-9 2,6-Bis-trimethylsilanyl-benzoic acid 2,2,2-trifluoro-ethyl ester 

Relevant academic research and scientific papers

Aryne 1,2,3,5-Tetrasubstitution Enabled by 3-Silylaryne and Allyl Sulfoxide via an Aromatic 1,3-Silyl Migration

Although benzyne has been well-known to serve as a synthon that can conveniently prepare various 1,2-difunctionalized benzenes, the sites other than its formal triple bond remain silent in typical benzyne transformations. An unprecedented aryne 1,2,3,5-tetrasubstitution was realized from 3-silylbenzyne and aryl allyl sulfoxide, the mechanistic pathway of which includes a regioselective aryne insertion into the SO bond, a [3,6]-sigmatropic rearrangement, and a thermal aromatic 1,3-silyl migration cascade.

Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization

Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C-O, C-S, and C-C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction modes involving both distal C-H bond functionalization and dearomatization.

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,

An Aryne-Based Route to Substituted Benzoisothiazoles

The combination of arynes, generated using fluoride from the corresponding 2-(trimethylsilyl)aryl triflates, and 3-hydroxy-4-aminothiadiazoles leads to the selective formation of 3-amino-substituted benzo[d]isothiazoles. Variation of the substitution pattern of the aryne precursor, and of the thiadiazole, is possible, with the target heterocycles being obtained in good to excellent yields. In all cases, use of 3-hydroxy-4-aminothiadiazoles leads to incorporation of the amino-substituent in the product heterocycle.

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