2114-42-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 5829, 1982 DOI: 10.1021/ja00385a066The Journal of Organic Chemistry, 39, p. 1168, 1974 DOI: 10.1021/jo00922a037Tetrahedron Letters, 33, p. 4545, 1992 DOI: 10.1016/S0040-4039(00)61308-4

InChI:InChI=1/C9H16/c1-2-6-9-7-4-3-5-8-9/h2,9H,1,3-8H2

Upstream product

• 106-95-6 allyl bromide 
• 931-50-0 cyclohexylmagnesium bromide 
• 187737-37-7 propene 
• 110-83-8 cyclohexene 
• 624-65-7 2-propynyl chloride 
• 110-82-7 cyclohexane 
• 107-05-1 3-chloroprop-1-ene 
• 931-51-1 cyclohexylmagnesiumchloride 
• 4786-20-3 but-2-enenitrile 
• 626-62-0 Cyclohexyl iodide 
• 76-63-1 allytriphenyltin 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 4143-42-4 (Z)-azomethane 
• 5296-64-0 allyl phenyl thioether 

Downstream Products

• 16529-03-6 cyclohexyl-3 epoxy-1,2 propane 
• 103-78-6 4-cyclohexyl-butan-2-one 
• 4361-28-8 3-cyclohexylpropanal 
• 187737-37-7 propene 
• 1678-92-8 propylcyclohexane 
• 103-65-1 phenylpropane 
• 65644-36-2 3-cyclohexylpropane-1,2-diol 
• 18899-70-2 3-Cyclohexyl-propyltrichlorsilan 
• 132539-51-6 (3-cyclohexylprop-1-ynyl)trimethylsilane 
• 111690-32-5 [2-Allyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester 
• 100690-17-3 2-acetylaminopropylcyclohexane 
• 100690-14-0 3-cyclohexyl-2-sulfooxy-propanesulfonic acid barium salt 
• 1860-41-9 4-cyclohexylbutyraldehyde 
• 2539-75-5 1-propylcyclohexene 

Relevant academic research and scientific papers

Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings

An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)2 or Fe(acac)2, Et2O, r.t.) to furnish various alkene and styrene derivatives. Mechanistic studies indicate the operation of a homotopic catalyst. The sequential combination of such iron-catalysed allylation with an iron-catalysed hydrogenation results in overall C(sp3)-C(sp3)-bond formation that constitutes an attractive alternative to challenging direct cross-coupling protocols with alkyl halides.

Visible-Light-Promoted Iron-Catalyzed C(sp2)–C(sp3) Kumada Cross-Coupling in Flow

A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution

A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.

Selective hydrogenolysis of phenols and phenyl ethers to arenes through direct C-O cleavage over ruthenium-tungsten bifunctional catalysts

Direct hydrogenolysis of the aromatic Csp2-O bonds in both phenols and phenyl ethers to form arenes selectively is a core enabling technology that can expand greatly the scope of chemical manufacture from biomass. However, conventional hydrogenolysis of phenols typically led to aromatic ring saturation instead of the cleavage of the Csp2-O bonds. Herein, we report a recyclable Ru-WOx bifunctional catalyst that showed high catalytic activities for the hydrogenolysis of a wide range of phenols and phenyl ethers, including dimeric lignin model compounds and the primitive phenols separated from pyrolysis lignin, to form arenes selectively in water. Preliminary mechanistic studies supported that the reactions occurred via a direct cleavage of the Csp2-O bonds and the concerted effects of the hydrogenating Ru sites and the Lewis acidic W sites are the key to such an unusual reactivity.

Copper-catalyzed selective semihydrogenation of terminal alkynes with hypophosphorous acid

A novel copper-catalyzed selective semihydrogenation of terminal alkynes using hypophosphorous acid as hydrogen donor took place efficiently to afford the corresponding alkenes in high yields. A broad range of substituted terminal aromatic and aliphatic alkenes, including terminal dienes and enynes bearing internal triple bonds, can be efficiently synthesized by this reaction.

Efficient and exceptionally selective semireduction of alkynes using a supported gold catalyst under a CO atmosphere

A new efficient method for chemo- and regio-selective semireduction of alkynes using CO/H2O as the hydrogen source catalyzed by gold supported on high surface area TiO2 was developed. A facile and practical synthesis of 1,2-dideuterioalkenes was also realized by using CO/D2O as the reducing agent. the Partner Organisations 2014.

Regioselective allene hydroarylation via one-pot allene hydrosilylation/Pd-catalyzed cross-coupling

Advances in hydroarylation have been achieved by the development of a one-pot regioselective allene hydrosilylation/Pd(0)-catalyzed cross-coupling protocol. The regioselectivity is primarily governed by N-heterocyclic carbene (NHC) ligand identity in the hydrosilylation step and is preserved in the subsequent cross-coupling reaction. This methodology affords streamlined access to functionalized 1,1-disubstituted alkenes with excellent regiocontrol. (Chemical Equation Presented).

High-yielding and rapid carbon-carbon bond formation from alcohols: Allylation by means of TiCl4

TiCl4 efficiently promotes high yield (80-99%) replacement of OH in tertiary, benzylic, and allylic alcohols, and even nonactivated secondary alcohols, by an allyl group. The reaction usually proceeds within minutes at room temperature. Georg Thieme Verlag Stuttgart. New York.

IRON BISPHENOLATE COMPLEXES AND METHODS OF USE AND SYNTHESIS THEREOF

The present application, relates to iron bisphenolate complexes and methods of use and synthesis thereof. The iron complexes are prepared from tridentate or tetradentate ligands of Formula I: wherein R1 and R2 are as defined herein. Also provided are methods and processes of using the iron bisphenolate complexes as catalysts in cross-coupling reactions and in controlled radical polymerizations.