111735-48-9

Upstream product

• 100-42-5 styrene 
• 762-16-3 octanoyl peroxide 
• 502494-89-5 octyl phosphonic acid benzyl ester methyl ester 
• 40630-63-5 octanesulfonyl fluoride 
• 100-52-7 benzaldehyde 
• 7795-95-1 octane-1-sulfonyl chloride 
• 4282-40-0 1-Iodoheptane 
• 21369-64-2 n-hexyllithium 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 22535-80-4 phenyl 1-octanesulfonate 
• 6172-97-0 octyl-phosphonic acid dimethyl ester 
• 103-54-8 cinnamyl acetate 
• 3761-92-0 n-hexylmagnesium bromide 
• 124-13-0 Octanal 

Downstream Products

• 1303568-37-7 C₁₇H₂₅BrO₂ 

Relevant academic research and scientific papers

Hindered organoboron groups in organic chemistry. 27. Preparations and some properties of alkylbis(2,6-dimethyl-4-methoxyphenyl)boranes ((DMP)2BR)

Akylbis(2,6-dimethyl-4-methoxyphenyl)boranes ((DMP)2BR) have been synthesized in an attempt to overcome the limitations of the steric hindrance approach to the production of boron stabilised carbanions. Anion production from (DMP)2BR, followed by alkylations and condensations with aldehydes are reported. Reduction of (DMP)2F with potassium hydride yields the corresponding hydroborate. Attempts to isolate (DMP)2BH were unsuccessful but the borane was readily trapped with alkynes, yielding alkenylboranes. The allyl derivative, (DMP)2BAllyl, was made and some of its reactions were investigated.

CROSS-COUPLIN REACTIONS BETWEEN SOME ALLYL, HOMOALLYL, AND HOMOPROPARGYL SUBSTRATES AND TRIALKYLALANES OR DIALKYL- AND DIARYL-MAGNESIUM DERIVATIVES

Trialkylalanes and dilkyl- and diaryl-magnesium derivatives can be cross-coupled with allyl ethers and esters, sulphides, and quaternized allylamines.The reactions proceed uncatalyzed either with mild conditions or in the presence of copper complex catalysts to result in high yields of mono- and di-olefins of various structures.The alkylation of homoallyl or homopropargyl tosylates by trialkylalanes is accompanied by cyclization, which leads to alkyl-substituted cyclopropanes. i.e. cyclobutanes and cyclopropylidenes.

Stereoselective Synthesis of E- and Z-Alkenes by the Boron-Wittig Reaction

Reactions of dimesitylboryl stabilised carbanions with aromatic aldehydes produce erythro-intermediates, which can be trapped by trimethylsilylation or trifluoroacetylation to give products which can yield E- or Z-alkenes in good overall yields in new and

Selective C-H chalcogenation of thiazoles: Via thiazol-2-yl-phosphonium salts

Thiazoles and benzothiazoles undergo regioselective C2-H chalcogenation via the sequence of thiazole C2-functionalization with phosphines to produce phosphonium salts which in turn react with S- and Se-centered nucleophiles to give products of C2-H chalco

Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones

Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.

Energy Transfer from CdS QDs to a Photogenerated Pd Complex Enhances the Rate and Selectivity of a Pd-Photocatalyzed Heck Reaction

This Article describes the design of a colloidal quantum dot (QD) photosensitizer for the Pd-photocatalyzed Heck coupling of styrene and iodocyclohexane to form 2-cyclohexylstyrene. In the presence of 0.05 mol % CdS QDs, which have an emission spectrum that overlaps the absorption spectrum of a key Pd(II)alkyl iodide intermediate, the reaction proceeds with 82% yield for the Heck product at 0.5 mol % loading of Pd catalyst; no product forms at this loading without a sensitizer. A radical trapping experiment and steady-state and transient optical spectroscopies indicate that the QDs transfer energy to a Pd(II)alkyl iodide intermediate, pushing the reaction toward a Pd(I) alkyl radical species that leads to the Heck coupled product, and suppressing undesired β-hydride elimination directly from the Pd(II)alkyl iodide. Functionalization of the surfaces of the QDs with isonicotinic acid increases the rate constant of this reaction by a factor of 2.4 by colocalizing the QD and the Pd-complex. The modularity and tunability of the QD core and surface make it a convenient and effective chromophore for this alternative mode of cooperative photocatalysis.

Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes

Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.

Stereodivergent synthesis of alkenes by controllable syn-/anti-fragmentation of β-hydroxysulfonyl intermediates

The reduction of the carbonyl group in acylated trifluoroethyl alkanesulfonates follows the Felkin-Ahn selectivity, and the so-formed diastereomeric β-hydroxysulfonyl intermediates undergo syn- and anti-fragmentation, depending on the reaction conditions. In effect, isomeric E- and Z-alkenes are formed in a stereodivergent manner, which mimics the mechanistic manifold of the Peterson olefination.

Photo-induced Decarboxylative Heck-Type Coupling of Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of Sacrificial Hydrogen Acceptors

1,2-Disubstituted alkenes such as vinyl arenes, vinyl silanes, and vinyl boronates are among the most versatile building blocks that can be found in every sector of chemical science. We herein report a noble-metal-free method of accessing such olefins through a photo-induced decarboxylative Heck-type coupling using alkyl carboxylic acids, one of the most ubiquitous building blocks, as the feedstocks. This transformation was achieved in the absence of external oxidants through the synergistic combination of an organo photo-redox catalyst and a cobaloxime catalyst, with H2 and CO2 as the only byproducts. Both control experiments and DFT calculations supported a radical-based mechanism, which eventually led to the development of a selective three-component coupling of aliphatic carboxylic acids, acrylates, and vinyl arenes. More than 90 olefins across a wide range of functionalities were effectively synthesized with this simple protocol.

Metal-Catalyzed Remote Functionalization of ω-Ene Unsaturated Ethers: Towards Functionalized Vinyl Species

The combined ruthenium-catalyzed chain walking with the nickel-catalyzed cross-coupling reaction of ω-alkenyl ethers provide a unique entry to functionalized vinyl species. This transformation illustrates the power and flexibility of remote functionalization by demonstrating the compatibility of two independent reactions involving unrelated sites.