910875-07-9

Upstream product

• 504-31-4 pyran-2-one 
• 159087-46-4 4,4,5,5-tetramethyl-2-trimethylsilanylethynyl-[1,3,2]dioxaborolane 
• 53097-28-2 (E/Z)-1-(phenylthio)buta-1,3-diene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1160757-30-1 (2-(trimethylsilyl)phenyl)boronic acid 
• 73183-34-3 bis(pinacol)diborane 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1016642-73-1 1,1-dimethyl-2,3-diphenyl-1H-benzo[b]silole 

Relevant academic research and scientific papers

Silylarene Hydrogenation: A Strategic Approach that Enables Direct Access to Versatile Silylated Saturated Carbo- and Heterocycles

We report a method to convert readily available silylated arenes into silylated saturated carbo- and heterocycles by arene hydrogenation. The scope includes alkoxy- and halosilyl substituents. Silyl groups can be derivatized into a plethora of functionalities and find application in organic synthesis, materials science, and pharmaceutical, agrochemical, and fragrance research. However, silylated saturated (hetero-) cycles are difficult to access with current technologies. The yield of the hydrogenation depends on the amount of the silica gel additive. This silica effect also enables a significant improvement of a previously disclosed method for the hydrogenation of highly fluorinated arenes (e.g., to all-cis-C6H6F6).

Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C?X (heteroatom) and C?C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.

Cobalt-catalyzed borylation of aryl halides and pseudohalides

We report the first Co-catalyzed borylation of aryl halides and pseudohalides with bis(pinacolato)diboron (B2pin2). The synthesis of two new Co(II) complexes of oxazolinylferrocenylphosphine ligands is described. Upon activation with LiMe, the Co complex catalyzes the borylation reactions of aryl bromides, iodides, sulfonates, arenediazonium salts, and even aryl chlorides under mild conditions, providing the borylated products in excellent to moderate yields and with high functional group tolerance.

Rhodium-catalyzed carbon-silicon bond activation for synthesis of benzosilole derivatives

A rhodium-catalyzed coupling reaction of 2-trimethylsilylphenylboronic acid with internal alkynes is developed for the synthesis of 2,3-disubstituted benzosilole derivatives. A range of functional groups, encompassing ketones, esters, amines, aryl bromides, and heteroarenes, are compatible, which provides rapid access to diverse benzosiloles. Sequential 2-fold coupling enables modular synthesis of asymmetrically substituted 1,5-dihydro-1,5-disila-s-indacene, a π-extended molecule of interest in organic electronics. In terms of the mechanism, the reaction involves cleavage of a C(alkyl)-Si bond in a trialkylsilyl group, which normally requires extremely harsh conditions for activation. Mechanistic studies, including effects of substituents, reveal that C-Si bond cleavage does not proceed through a hypercoordinated silicon species, but rather through a rhodium-mediated activation process. The potential use of the reaction in catalytic asymmetric synthesis of Si-chiral benzosiloles is also demonstrated.

Ambient-temperature cobalt-catalyzed cycloaddition strategies to aromatic boronic esters

Figure presented The room-temperature cobalt-catalyzed [4 + 2] cycloaddition of alkynylboronates and 1,3-dienes provides a convenient and general method for the synthesis of benzene-based aromatic boronic esters. Two complementary aromatization strategies involving in situ elimination and DDQ oxidation were explored, with the latter finding more generality. Finally, the potential of this technique to generate highly functionalized biaryls has been demonstrated via the synthesis of chiral (racemic) DMAP catalysts.

An alkynylboronic ester cycloaddition route to functionalised aromatic boronic esters

A series of functionalised aromatic boronic esters have been prepared via the regioselective cycloaddition of 2-pyrones with alkynylboronates. The Royal Society of Chemistry 2006.