1588-44-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 20, p. 3425, 1979 DOI: 10.1016/S0040-4039(01)95426-7

Upstream product

• 1462-75-5 3-phenylpropylmagnesium bromide 
• 106-95-6 allyl bromide 
• 637-59-2 1-Bromo-3-phenylpropane 
• 2695-47-8 6-Bromo-1-hexene 
• 100-47-0 benzonitrile 
• 113328-06-6 6-methylseleno-6-phenylhex-1-ene 
• 14996-78-2 2-phenylcycloheptanone 
• 202932-64-7 1-phenyl-5-hexen-3-one 
• 4119-41-9 1-iodo-3-phenylpropan 
• 2622-05-1 allylmagnesium bromide 
• 36884-28-3 5-phenyl-1-pentanal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 10521-91-2 5-phenylpentan-1-ol 
• 1119-51-3 bromopentene 

Downstream Products

• 339566-88-0 1,10-Diphenyl-5-decen 
• 129169-51-3 6-phenyl-1-phenylthiohexane 
• 105474-17-7 (5-bromo-hexyl)-benzene 
• 934473-28-6 2-(4-phenyl-butyl)-oxirane 
• 934473-33-3 tert-butyl-dimethyl-[1-(4-phenyl-butyl)-but-3-enyloxy]-silane 
• 934473-29-7 tert-butyl-dimethyl-(1-oxiranylmethyl-5-phenyl-pentyloxy)-silane 
• 934473-27-5 tert-butyl-dimethyl-(1-oxiranylmethyl-5-phenyl-pentyloxy)-silane 
• 934473-34-4 (2R,4R)-4-(tert-butyldimethylsilyloxy)-8-phenyloctane-1,2-diol 
• 1026938-84-0 3-(tert-butyl-dimethyl-silanyloxy)-6-[2,2-dimethyl-6-(4-phenyl-butyl)-[1,3]dioxan-4-yl]-hex-4-enal 
• 934473-31-1 3-(tert-butyl-dimethyl-silanyloxy)-6-[2,2-dimethyl-6-(4-phenyl-butyl)-[1,3]dioxan-4-yl]-hex-4-en-1-ol 
• 934473-30-0 6-[2,2-dimethyl-6-(4-phenyl-butyl)-[1,3]dioxan-4-yl]-1-(4-methoxy-benzyloxy)-hex-4-en-3-ol 
• 934473-26-4 1-(4-methoxy-benzyloxy)-13-phenyl-tridec-4-yne-3,7,9-triol 
• 934473-36-6 6-[2,2-dimethyl-6-(4-phenyl-butyl)-[1,3]dioxan-4-yl]-1-(4-methoxy-benzyloxy)-hex-4-yn-3-ol 
• 934473-25-3 5-(tert-butyl-dimethyl-silanyloxy)-8-[2,2-dimethyl-6-(4-phenyl-butyl)-[1,3]dioxan-4-yl]-octa-2,6-dienoic acid methyl ester 

Relevant academic research and scientific papers

Cobalt-catalyzed coupling reaction of alkyl halides with allylic grignard reagents

Facile construction of quaternary carbon centers: The cobalt-catalyzed coupling reaction of not only primary and secondary but also tertiary alkyl halides with allylic Grignard reagents proceeds smoothly (see scheme; dppp = 1,3-bis(diphenylphosphanyl)prop

Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents

Iron nanoparticles, either formed in situ stabilized by 1,6-bis(diphenylphosphino)hexane or polyethylene glycol (PEG), or preformed stabilized by PEG, are excellent catalysts for the cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens and they also prove effective in a tandem cyclization/cross- coupling reaction. The Royal Society of Chemistry 2006.

Synthesis of alkyl sulfones from alkenes and tosylmethylphosphonium iodide through photo-promoted cc bond formation

A new synthetic method for alkyl sulfones through CC bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)3. It undergoes regioselective 1,2-addition across the carboncarbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C6F5SH, producing an alkyl sulfone with one-carbon extension.

Synergistic Hydrocobaltation and Borylcobaltation Enable Regioselective Migratory Triborylation of Unactivated Alkenes

The structural diversity of sp3-triorganometallic reagents enhances their potentiality in the modular construction of molecular complexity in chemical synthesis. Despite significant achievements on the preparation of sp3 1,1,1- and 1,1,2-triorganometallic B,B,B-reagents, catalytic approaches that enable the installation of multiple boryl groups at skipped carbons of unactivated alkenes still remain elusive. Herein, we report a cobalt-catalyzed selective triborylation reaction of unactivated alkenes to access synthetically versatile 1,1,3-triborylalkanes. This triborylation protocol provides a general platform for regioselective trifunctionalization of unactivated alkenes, and its utility is highlighted by the synthesis of various value-added chemicals from readily accessible unactivated alkenes. Mechanistic studies, including deuterium-labelling experiments and evaluation of potential reactive intermediates, provide insight into the experimentally observed chemo- and regioselectivity.

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h

Transition Metal-Free sp3?sp3 Carbon-Carbon Coupling between Benzylboronic Esters and Alkyl Bromides

A transition metal-free coupling reaction of benzylboronic esters and alkyl halides has been developed. Both alkyl bromides and alkyl iodides were found to be competent substrates with the nucleophilic boronate intermediate generated from the combination of benzylboronic ester and an alkyllithium. Good chemoselectivity was observed for the reaction with the alkyl bromide in substrates with a second electrophile present. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.

Visible Light/Tertiary Amine Promoted Synergistic Hydroxydifluoroacetamidation of Unactivated Alkenes under Air

An efficient and novel method for regioselective hydroxydifluoroacetamidation of alkenes with bromodifluoroacetamides has been achieved via a tandem radical pathway mediated by photoredox catalysis under metal-free conditions. This transformation proceeded smoothly in the presence of Rhodamine 6G, affording a series of α,α-difluoro-γ-hydroxyacetamides in moderate to excellent yields. The significant advantages of this protocol are the low-cost photocatalyst, readily available starting materials, synthetic convenience, and wide functional group compatibility.

General C(sp2)-C(sp3) Cross-Electrophile Coupling Reactions Enabled by Overcharge Protection of Homogeneous Electrocatalysts

Cross-electrophile coupling (XEC) of alkyl and aryl halides promoted by electrochemistry represents an attractive alternative to conventional methods that require stoichiometric quantities of high-energy reductants. Most importantly, electroreduction can readily exceed the reducing potentials of chemical reductants to activate catalysts with improved reactivities and selectivities over conventional systems. This work details the mechanistically-driven development of an electrochemical methodology for XEC that utilizes redox-active shuttles developed by the energy-storage community to protect reactive coupling catalysts from overreduction. The resulting electrocatalytic system is practical, scalable, and broadly applicable to the reductive coupling of a wide range of aryl, heteroaryl, or vinyl bromides with primary or secondary alkyl bromides. The impact of overcharge protection as a strategy for electrosynthetic methodologies is underscored by the dramatic differences in yields from coupling reactions with added redox shuttles (generally >80%) and those without (generally 20%). In addition to excellent yields for a wide range of substrates, reactions protected from overreduction can be performed at high currents and on multigram scales.