91034-75-2

Upstream product

• 776-76-1 methyldiphenylsilane 
• 36306-56-6 crotylmagnesium bromide 

Downstream Products

• 123376-75-0 (R*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one 
• 123376-75-0 (S*)-3-((R*)-but-3-en-2-yl)cyclohexan-1-one 

Relevant academic research and scientific papers

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

METHODS OF BORYLATION AND USES THEREOF

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

Cobalt-catalyzed isomerization of 1-alkenes to (E)-2-alkenes with dimethylphenylsilylmethylmagnesium chloride and its application to the stereoselective synthesis of (E)-alkenylsilane

Treatment of 1-alkenes with dimethylphenylsilylmethylmagnesium chloride in the presence of a cobalt-NHC complex in dioxane at 50°C or higher provides the corresponding (E)-2-alkenes selectively. The isomerization is applicable to the stereoselective synth

Stereospecificity in the silicon tethered α-(methyl)allylation of aldehydes

Heating E- and Z-crotyl(diphenyl)silyloxy aldehydes, in the absence of an added catalyst, results in sterospecific intramolecular allyl transfer with moderate to high stereoselectivity. The successful preparation of suitable substrates was described to test the given proposal. This paper reports their behavior under both Lewis acidic and thermal conditions.

SELECTIVE SYNTHESIS OF (E)-CROTYLSILANES BY REACTION OF CROTYLMAGNESIUM BROMIDE WITH HYDROSILANES IN THE PRESENCE OF DICHLORONIKKEL(II)

Dichloronickel(II) was found to be an effective catalyst for the reaction of crotylmagnesium bromide with hydrosilanes to give (E)-crotyl-silanes selectively.