57024-90-5

Upstream product

• 629-27-6 1-Iodooctane 
• 3017-71-8 (E)-2-bromobut-2-ene 
• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 
• 3017-68-3 (Z)-2-Bromo-2-butene 
• 111-66-0 oct-1-ene 
• 3017-69-4 2-methyl-1-propenylbromide 
• 13294-71-8 2-bromo-but-2-ene 
• 38841-98-4 n-octylmagnesium chloride 

Relevant academic research and scientific papers

Asymmetric Synthesis of Dihydropyranones via Gold(I)-Catalyzed Intermolecular [4+2] Annulation of Propiolates and Alkenes

Intermolecular asymmetric gold catalysis involving alkyne activation presents a significant challenge due to its distinct mechanistic mode from other metals. Herein, we report a highly enantioselective synthesis of α,β-unsaturated δ-lactones from [4+2] annulation of propiolates and alkenes in upto 95 percent ee. Notably, for the desired chiral recognition, the choice of 1,1,2,2-tetrachloroethane as solvent was found to be crucial. Furthermore, an anionic surfactant (sodium dodecyl sulfate) improved the product selectivity in the divergence of the cyclopropyl gold carbene intermediate.

Utilization of a Trimethylsilyl Group as a Synthetic Equivalent of a Hydroxyl Group via Chemoselective C(sp3)-H Borylation at the Methyl Group on Silicon

A conversion of trimethylsilylalkanes into the corresponding alcohols is established based on an iridium-catalyzed, chemoselective C(sp3)-H borylation of the methyl group on silicon. The (borylmethyl)silyl group formed by C(sp3)-H borylation is treated with H2O2/NaOH, and the resulting (hydroxymethyl)silyl group is converted into a hydroxyl group by Brook rearrangement, followed by oxidation of the resulting methoxysilyl group under Tamao conditions. An alternative route proceeding through the formylsilyl group formed from a (hydroxymethyl)silyl group by Swern oxidation is also established. The method is applicable to substituted trimethylsilylcycloalkanes and 1,1-dimethyl-1-silacyclopentane for conversion into the corresponding stereodefined cycloalkyl alcohols and 1,4-butanediol.

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

Palladium-Catalyzed Inter- and Intramolecular Cross-Coupling Reactions of B-Alkyl-9-borabicyclononane Derivatives with 1-Halo-1-alkenes or Haloarenes. Syntheses of Functionalized Alkenes, Arenes, and Cycloalkenes via a Hydroboration-Coupling Sequence

The cross-coupling reaction of B-alkyl-9-borabicyclononanes (B-R-9-BBN), readily obtainable from alkenes by hydroboration, with 1-halo-1-alkenes or haloarenes in the presence of a catalytic amount of PdCl2(dppf) and bases, such as sodium hydroxide, potassium carbonate, and phosphate, gave the corresponding alkenes or arenes.Because the reaction is tolerant of a variety of functionalities on either coupling partner, stereochemically pure functionalized alkenes and arenes can be obtained under mild conditions.The utility of the reaction was demonstrated by the stereoselective synthesis of 1,5-alkadienes (7 and 8) and the extension of a side chain in a steroid (11).The hydroboration of haloalkadienes (12), followed by the intramolecular cross-coupling, gave a short-step procedure for synthesis of cycloalkenes, benzo-fused cycloalkenes, and exocyclic alkenes (14 and 16).

PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF B-ALKYL-9-BBN OF TRIALKYLBORANES WITH ARYL AND 1-ALKENYL HALIDES

The reactions of trialkylboranes or B-alkyl-9-BBN with aryl and 1-alkenyl halides take place readily in the presence of PdCl2(dppf) and sodium hydroxide or methoxide to afford alkylatad arenes and alkenes in excellent yields.