36601-47-5

Upstream product

• 16029-98-4 trimethylsilyl iodide 
• 578-57-4 2-bromoanisole 
• 109-72-8 n-butyllithium 
• 75-77-4 chloro-trimethyl-silane 
• 84998-58-3 Diisopropylphosphinigsaeure-o-bromphenylester 
• 84998-59-4 2-(2-Bromo-phenoxy)-[1,3,2]dioxaphospholane 
• 84998-60-7 2-(2-Bromo-phenoxy)-[1,3,2]dioxarsolane 
• 95-56-7 2-hydroxybromobenzene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 23647-50-9 BrC₆H₄OSn(C₂H₅)3 
• 108-95-2 phenol 
• 4039-32-1 lithium hexamethyldisilazane 
• 107-46-0 Hexamethyldisiloxane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 15288-53-6 o-(trimethylsilyl)phenol 
• 57263-24-8 2-[1-hydroxy-2,2,4,4-tetramethyl-3-(4-pyridin-2-yl-piperazin-1-yl)-cyclobutyl]-phenol 
• 89466-08-0 2-hydroxyphenyl boronic acid 
• 1373397-21-7 2-(trimethylsilyl)phenyl imidazol-1-sulfonate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.

Preparation method of hydroxyphenylboronic acid

The invention discloses a preparation method of hydroxyphenylboronic acid, which belongs to the technical field of boric acid synthesis in medical intermediates. The method comprises the following steps: starting from bromophenol, carrying out BOC, trimethylsilyl or benzyl protection, forming a Grignard reagent, reacting with borate, or carrying out one-pot reaction with borate and n-butyllithium,and hydrolyzing to obtain hydroxyphenylboronic acid. According to the invention, cheap and easily available protecting groups are adopted, so that the protecting groups are easy to remove during boronation reaction hydrolysis, industrial amplification is easy to realize, batch production is carried out on the scale of dozens of kilograms, and the process stability is good.

Stereoretentive Ring-Opening Metathesis Polymerization to Access All- cis Poly(p-phenylenevinylene)s with Living Characteristics

Poly(p-phenylenevinylene)s (PPVs), a staple of the conductive polymer family, consist of alternating alkene and phenyl groups in conjugation. The physical properties of this organic material are intimately linked to the cis/trans configuration of the alkene groups. While many synthetic methods afford PPVs with all-trans stereochemistry, very few deliver the all-cis congeners. We report herein a synthesis of all-cis PPVs with living characteristics via stereoretentive ring-opening metathesis polymerization (ROMP). Exquisite catalyst control allows for the preparation of homopolymers or diblock copolymers with perfect stereoselectivity, narrow dispersities, and predictable average molar masses. All-cis PPVs can then serve as light-responsive polymers through clean photoisomerization of the stilbenoid units.

Radical Truce-Smiles reactions on an isoxazole template: Scope and limitations

The use of TiCl3-HCl as promotor in the radical Truce-Smiles reactions of 2-(((3,5-dimethylisoxazol-4-yl)sulfonyl)oxy)benzenediazonium salts has been investigated in detail. During these reactions the desired Truce-Smiles rearrangement (via an ipso-substitution reaction) is accompanied by the formation of a number of by-products including dihydrobenzo[5,6][1,2]oxathiino[3,4-d]isoxazole 4,4-dioxides, dioxidobenzo[e][1,2]oxathiin-3-yl)ethan-1-ones, anilines and chloroaromatics. Replacing TiCl3-HCl by Cu(NO3)2-Cu2O as reductant in these reactions was found to afford broadly comparable product distributions. Competition and radical clock experiments also provide an indication of the relative susceptibility of the isoxazole nucleus towards attack by aryl radicals.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

A facile route to 1: H- A nd 2 H-indazoles from readily accessible acyl hydrazides by exploiting a novel aryne-based molecular rearrangement

Herein we report the transformation of readily synthesised acyl hydrazides into 2-hydrazobenzophenones via a novel molecular rearrangement pathway using aryne chemistry. The developed reaction protocol is performed under relatively mild conditions and is

Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides

The aryne insertion into "S-O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethe

(3 + 2)-Annulation of p-Quinamine and Aryne: A Strategy to Construct the Multisubstituted Hydrocarbazoles

A strategy for the synthesis of multisubstituted hydrocarbazoles has been developed through (3 + 2)-annulation of p-quinamines and arynes. In this way, new analogs of hydrocarbazoles with quaternary carbon center can be synthesized in satisfactory yield under mild conditions. Furthermore, this (3 + 2)-annulation can be easily scaled-up, and the products can be modified through simple transformation.

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.

Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines

The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.