74630-59-4

Upstream product

• 590-18-1 (Z)-2-Butene 
• 629-05-0 n-octyne 
• 13317-63-0 (di-s-butyl)bromoborane 
• 42843-49-2 (Z)-1-bromo-1-octene 
• 15366-08-2 s-butylmagnesium chloride 

Relevant academic research and scientific papers

Iron thiolate complexes: Efficient catalysts for coupling alkenyl halides with alkyl grignard reagents

Ironing out the kinks: Efficient new catalytic systems based on iron thiolates are described for the iron-catalyzed cross-coupling of alkyl Grignard reagents with alkenyl halides (see scheme). The reaction is highly chemo- and stereoselective. With this new procedure, the use of N-methylpyrrolidone as a co-solvent is no longer required. Copyright

Photoinduced metalation of nonactivated C-Cl bonds with samarium diiodide: Synthesis of alkenes with high (Z)-selectivity through β-elimination reactions

(Chemical Equation Presented) The photoinduced metalation of nonactivated C-Cl bonds of O-acetyl chlorohydrins is promoted by samarium diiodide. As a result of this, β-elimination of O-acetyl chlorohydrins is achieved, affording the corresponding (Z)-alkenes with total or high stereoselectivity.

Vinylic Organoboranes. 9. A General Stereospecific Synthesis of (Z)- and (E)-Disubstituted Alkenes via Organoboranes

A general and stereospecific synthesis of (Z)-disubstituted alkenes using mono- and dihaloboranes is presented.The hydridation of dialkylhaloboranes in the presence of 1-alkynes provides the corresponding dialkylvinylboranes (1), representing the first general synthesis of such derivatives.Treatment with iodine in the presence of sodium methoxide induces the migration of one of the alkyl groups from boron to the adjacent carbon, followed by a rapid deiodoboronation to afford (Z)-disubstituted alkenes (2) in high yields.Similarly, the hydroboration of 1-alkynes with alkyl bromoboranes (R1BHBr*SMe2, 4) followed by iodination in the presence of sodium methoxide in methanol affords (Z)-disubstituted alkenes (2) in good yields.Both procedures constitute a general one-pot synthesis of (Z)- disubstituted alkenes from an alkene and 1-alkyne.A simple synthesis of Muscalure (7), the sex pheromone of the housefly (Musca domestica), is achieved in good yields.An alternative general stereospecific synthesis of (Z)- and (E)-disubstituted alkenes based on alkenylboronic esters is also described.

IODINE INDUCED TRANSFER OF DIALKYLVINYLBORANES PRODUCED BY THE HYDRIDATION OF DIALKYLHALOBORANES IN THE PRESENCE OF 1-ALKYNES. GENERALIZATION OF THE ZWEIFEL cis-ALKENE SYNTHESIS

Dialkylvinylboranes, prepared conveniently via the hydridation of dialkylhaloboranes in the presence of terminal alkynes, react with iodine in the presence of base at reduced temperatures to form teh corresponding cis-disubstituted alkenes.This development greatly increases the generality of the elegant Zweifel cis-olefin synthesis.