1048371-87-4

Upstream product

• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 97483-86-8 3-methoxyphenyl 2,2-dimethylpropionate 
• 617-86-7 triethylsilane 
• 100-66-3 methoxybenzene 
• 586-38-9 3-Methoxybenzoic acid 
• 1711-05-3 m-anisoyl chloride 
• 994-30-9 triethylsilyl chloride 
• 85630-18-8 N,N-diethyl-O-(4-methoxyphenyl)carbamate 
• 1379516-28-5 C₁₈H₃₁NO₃Si 
• 766-85-8 3-methoxy-1-iodobenzene 

Relevant academic research and scientific papers

Nickel-Catalyzed Decarbonylative Silylation, Borylation, and Amination of Arylamides via a Deamidative Reaction Pathway

A nickel-catalyzed decarbonylative silylation, borylation, and amination of amides has been developed. This new methodology allows the direct interconversion of amides to arylsilanes, arylboronates, and arylamines and enables a facile route for carbon-heteroatom bond formations in a straightforward and mild fashion.

Intermolecular C-H Silylation of Arenes and Heteroarenes with HSiEt3 under Operationally Diverse Conditions: Neat/Stoichiometric and Acceptor/Acceptorless

Efficient protocols for Rh-catalyzed intermolecular C-H silylation of unactivated arenes and heteroarenes are disclosed. The silylations are catalyzed by a Rh-complex (2 mol %) derived in situ from commercially available Rh(nbd)2BF4 and (S,S)-i-Pr-BPE (L3) with Et3SiH in the presence of hydrogen acceptor under either neat (excess of arene) or stoichiometric conditions. The regioselectivity is determined mainly by the steric bulk of the substituents and by the electronic effect as an ancillary factor. In addition, our preliminary result shows that the current protocol catalyzes the silylation of arenes in the absence of hydrogen acceptors.

A mild Ni/Cu-catalyzed silylation via C -O cleavage

A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols is described. This transformation is characterized by its wide scope and mild conditions, providing a direct access to synthetically versatile silylated compounds. The protocol allows for the coupling of C(sp 2)-O and even C(sp3)-O bonds with similar efficiency.

Cine substitution of arenes using the aryl carbamate as a removable directing group

An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionalization. The removal of aryl carbamates is achieved by employing an air-stable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.

Direct and selective arylation of tertiary silanes with rhodium catalyst

(Chemical Equation Presented) We have developed a convenient and efficient approach to the arylation of tertiary silanes under mild conditions. A variety of arylsilanes were synthesized in a one-step process with good to excellent yields in the presence of a rhodium catalyst with a base. The reaction was highly solvent dependent, and amides were the most effective of the various solvents used. This common catalyst system is highly tolerant of the various sensitive functional groups on the substrates, which might be difficult to extract by other methods. The rhodium-promoted silylation of aryl halides with electron-donating groups occurred more efficiently than the silylation of aryl halides substituted with electron-withdrawing groups. Heteroaromatic halides were also found to be readily silylated with tertiary silanes. The successful application of this reaction to the synthesis of a TAC-101 analogue, which is a trialkylsilyl-containing synthetic retinoid benzoic acid derivative with selective binding affinity for retinoic acid receptor-α, is also described.