110897-35-3

Upstream product

• 109-72-8 n-butyllithium 
• 591-50-4 iodobenzene 
• 91083-32-8 <(Z)1-Bromo-1-hexenyl>diisopropoxyborane 
• 591-51-5 phenyllithium 
• 105763-18-6 (Z)-2-(1-butyl-1-hexenyl)-1,3,2-dioxaborinane 
• 661488-99-9 Dibutyl-((E)-1-butyl-2-phenylsulfanyl-hex-1-enyl)-borane 
• 693-02-7 hex-1-yne 
• 137298-82-9 (Z)-5-(phenylthio)dec-5-ene 
• 106865-24-1 (Z)-5-Iodo-5-decene 
• 104293-08-5 (5E)-5-iodo-dec-5-ene 

Relevant academic research and scientific papers

Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates: Controlled syntheses of trisubstituted olefins from 1-alkynes

The reaction of 1-alkynyltrialkyl borates with sulfenyl, selenenyl and tellurenyl halides produces β-chalcogeno alkenylboranes in good yields, with a cis relationship between the boron and the chalcogen moities. Protodeborylation of these compounds by acetic acid, or by a transmetalation-protonolysis sequence, leads to vinyl chalcogenides, which can be converted to alkenes by means of a nickel catalyzed coupling with Grignard reagents. Since the last two steps occur with retention of the stereochemistry, the overall sequence represents a highly regio- and stereoselective olefin synthesis.

TRANSITION METAL ?-COMPLEXES IN ORGANIC SYNTHESIS 5. CROSS-COUPLING OF ORGANOMANGANESE COMPOUNDS WITH ALKENYL IODIDES

Aryl organomanganese compounds ArMnX and Ph3MnLi (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-BrC6H4, α-naphthyl; X = Cl, Br) react with alkenyl iodides RR1C=CR2I (R = H, Pr, Bu, i-Bu, C6H13, CH2=CHCH2, Ph; R1 = H, Pr, C5H11; R2 = H, Pr, SiMe3) in THF at 0-20 deg C to give cross-coupling products RR1C=CR2Ar in high yields.

Vinylic Organoboranes. 11. A Highly Stereospecific and Regiospecific Synthesis of Trisubstituted Alkenes via Organoboranes

A highly stereospecific synthesis of trisubstituted alkenes using (E)- and (Z)-2-(1-substituted-1-alkenyl)-1,3,2-dioxaborinanes is presented. (E)-2-(1-Substituted-1-alkenyl)-1,3,2-dioxaborinanes (1), as described previously, readily react with organolithium or Grignard reagents in diethyl ether at -78 deg C to form the corresponding "ate" complexes.Treatment of these "ate" complexes with iodine in methanol induces the migration of the alkyl group from boron to the adjacent carbon, followed by a base-induced deiodoboronation to afford stereodefined trisubstituted alkenes in good yields (50-82percent) and in excellent stereochemical purities (97percent).Similarly (Z)-2-(1-substituted-1-alkenyl)-1,3,2-dioxaborinanes (2), easily obtainable by a previous procedure, react with organolithium or Grignard reagents, followed by treatment with iodine and base, to produce the stereoisomeric trisubstituted alkenes in good yields (65-82percent) and in excellent isomeric purites (97percent).These two procedures provide a convenient route to any of the six possible trisubstituted alkenes, R1CH=CR2R3.

Stereo- and Regiospecific Synthesis of Trisubstituted Alkenes via the Palladium-catalyzed Cross-coupling Reaction of Diisopropyl (E)-(1-Alkyl-1-alkenyl)boronates with Organic Halides

The reaction of diisopropyl (Z)-(1-bromo-1-alkenyl)boronates readily obtainable, with organolithiums and bases takes place readily to give (E)-(1-organo-1-alkenyl)boronates, the cross-coupling of which with various organic halides proceeds smoothly in the presence of Pd-catalyst and base to afford stereodefinied trisubstituted alkenes in good yields.