89656-98-4

Upstream product

• 3017-69-4 2-methyl-1-propenylbromide 
• 931-51-1 cyclohexylmagnesiumchloride 
• 24371-94-6 cyclohexylmercury chloride 
• 23010-28-8 2,2-dimethylethenylmercury bromide 
• 542-18-7 cyclohexyl chloride 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 
• 626-62-0 Cyclohexyl iodide 
• 108-85-0 1-bromocyclohexane 
• 20687-01-8 1-iodo-2-methylpropene 
• 90047-75-9 1-Iodo-8-methyl-6,7-nonadiene 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 91975-66-5 2,2-Dimethyl-3-trans-cyclohexyl-cyclopropan-carbonsaeure-⁽¹⁾-methylester 

Relevant academic research and scientific papers

Direct Cross-Coupling of Allylic C(sp3)?H Bonds with Aryl- and Vinylbromides by Combined Nickel and Visible-Light Catalysis

An efficient protocol for the direct allylic C(sp3)?H bond activation of unactivated tri- and tetrasubstituted alkenes and their functionalization with aryl- and vinylbromides by nickel and visible-light photocatalysis has been developed. The method allows C(sp2)?C(sp3) formation under mild reaction conditions with good functional-group tolerance and excellent regioselectivity.

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

Iron-catalyzed negishi coupling toward an effective olefin synthesis

A selective Iron-catalyzed cross-coupling of alkyl halldes with alkenylzinc reagents Is described. Primary and secondary alkyl chlorides, bromides, and iodides take part In the reaction to give the corresponding olefins In good to excellent yields In a stereospecific manner. High functional group compatibility Is also demonstrated by using combinations of substrates possessing rather reactive substituents.

Iron-catalyzed cross-coupling of alkyl halides with alkenyl Grignard reagents

(Chemical Equation Presented) Cheap and safe: An iron-catalyzed cross-coupling reaction between alkyl halides and alkenyl Grignard reagents is described. This C-C bond coupling reaction is promoted by the cheap and nontoxic FeCl3 and displays good tolerance against various functional groups.

Iron-catalyzed alkylation of alkenyl grignard reagents

The first iron-catalyzed cross-coupling reaction between alkenyl Grignard reagents and n- or s-alkyl bromides is described. The reaction is stereoselective and takes place in the presence of 5 mol % of [Fe(acac) 3MEDA/HMTA] (1:2:1) under very mild conditions (THF, 0°C, 45 min).

Enantioselective [2 + 2] cycloaddition of unactivated alkenes with α-acyloxyacroleins catalyzed by chiral organoammonium salts

We report the first example of an organocatalytic enantioselective [2 + 2] cycloaddition reaction of unactivated alkenes with α-acyloxyacroleins to give optically active 1-acyloxycyclobutanecarbaldehydes and subsequent ring expansion to give optically active 2-hydroxycyclopentanone derivatives. Organoammonium salt, H-L-Phe-L-Leu-N(CH2CH2)2-reduced triamine?2.6HNTf2, is a highly effective chiral catalyst for the above enantioselective [2 + 2] cycloaddition. Thus, we have developed a novel and useful formal enantioselective [2 + 3] cycloaddition through two steps. Copyright

Control of regioselectivity by the lone substituent through steric and electronic effects in the nitrosoarene ene reaction of deuterium-labeled trisubstituted alkenes

For the ene reaction of 4-nitronitrosobenzene (ARNO) with a variety of primary and secondary lone alkyl-substituted substrates, the twix/twin regioselectivity is constant at about 85:15. In contrast, for the lone tert-butyl group and for lone aryl substituents, the twix regioisomer is obtained exclusively. These regioselectivities have been rationalized in terms of steric interactions and coordination between the enophile and the substrates in the transition states of the first reaction step.

Highly stereo and chemoselective iron-catalyzed alkenylation of organomagnesium compounds

In the presence of Fe(acac)3, Grignard reagents react readily with alkenyl halides (X = I, Br or Cl) in a THF/NMP mixture to give the cross-coupling products in high yields with an excellent stereoselectivity (≤99.5%). The scope of the reaction is very broad since a vast array of functional groups are tolerated (esters, nitriles, aromatic or aliphatic halides and even ketones). The procedure reported herein is an interesting alternative to the classical Pd- or Ni-catalyzed reactions, especially for preparative organic chemistry.

Cyclization of ω-Allenyl Organometallic Reagents

Allenyl organometallic reagents of type R2C=C=CH(CH2)nCH2M undergo cyclization at the central allenic carbon for n=2 (M=Li) and at the near allenic carbon for n=3 (M=CuCNLi) to provide cyclopentane systems; little cyclization was observed for the n=4 systems (M=Li, CuCNLi). Key words: Allene; cyclization; organometallic; organolithium; cuprate.

Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals

The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.