16538-48-0

Upstream product

• 592-41-6 1-hexene 
• 110-83-8 cyclohexene 
• 37609-12-4 (E)-hex-1-enyldicyclohexylborane 
• 110-82-7 cyclohexane 
• 693-02-7 hex-1-yne 
• 1568-65-6 bis(cyclohexanyl)borane 
• 36140-19-9 dicyclohexylboron chloride 
• 19094-29-2 2-(pentane-1-sulfonyl)-benzothiazole 
• 2043-61-0 cyclohexanecarbaldehyde 
• 203317-33-3 5-(pentane-1-sulfonyl)-1-phenyl-1H-1,2,3,4-tetrazole 
• 13154-12-6 (Z)-1-bromohex-1-ene 
• 931-51-1 cyclohexylmagnesiumchloride 
• 67532-06-3 (E)-1-bromo-1-cyclohexyl-1-hexene 
• 273730-80-6 1-tert-butyl-5-(pentane-1-sulfonyl)-1H-tetrazole 

Relevant academic research and scientific papers

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.

Molecular addition compounds. 6. Addition compounds of ethylenediamine with boron trifluoride and dialkylboranes

Ethylenediamine (EDA) reacts readily with boron trifluoride in ether to give the insoluble mono adduct NH2CH2CH2NH2·BF3. The amine also reacts with dialkylboranes in a 1:2 molar ratio to provide the bis adducts EDA·2BHR2. The latter adducts are quite stable and can be stored at 0°C without detectable isomerization or redistribution. In ether or THF, boron trifluoride readily and quantitatively removes EDA from these adducts liberating the free dialkylboranes. Thus this procedure provides a new valuable means for storing dialkylboranes as their stable EDA adducts, with rapid regeneration of the parent dialkylborane as desired.

Vinylic Organoboranes. 6. A General Synthesis of (E)-Disubstituted Alkenes or Ketones via the (E)-(1-Substituted-1-alkenyl)boronic Esters

Development of a general stereospecific synthesis of (E)-disubstituted alkenes utilizing a variety of hydroborating agents such as monohaloborane, thexylborane, thexylchloroborane, and dibromoborane is discussed.Hydroboration of 1-halo-1-alkynes with dial

Reaction of (Z)-1-bromoalk-1-enyldialkylboranes with DMSO: Regio- and stereo-selective formation of internal (E)-alkenyl bromides

Treatment of (Z)-1-bromoalk-1-enyldialkylboranes 1 with DMSO results in 1,2-migration of an alkyl group from the boron to the α-carbon without elimination of bromine to give internal (E)-alkenyl bromides 2 with excellent stereoselectivity (>99%).

A stereoselective synthesis of 1,2-disubstituted alkenyl selenides via hydroboration-iodination of internal alkylselenoacetylenes with dicyclohexylborane

Selenoalkenyldicyclohexylboranes, prepared conveniently via hydroboration of internal alkylselenoacetylenes with dicyclohexylborane followed by iodination under basic conditions, produce cis/trans 1,2-disubstituted alkenyl selenides (1 and 2), which provide a general method for synthesis of cis/trans disubstituted alkenyl selenides containing a cyclohexyl group.

Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides

A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.

1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones

The stability and the stereoselectivity of newly prepared n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high yields were obtained from the reaction with aromatic aldehydes and α,β-unsaturated aldehydes. The selectivity of 1a was not so sensitive to the change of base counter ion compared with the PT sulfone 1b. The reaction of the MT sulfones having either ethyl or a longer alkyl chain also gave E-alkenes selectively in high yields.

Copper-catalyzed semihydrogenation of internal alkynes with molecular hydrogen

A copper-catalyzed system using a commercially available simple N-heterocyclic carbene ligand under atmospheric pressure of H2 (1 atm, balloon) enables the semihydrogenation of internal alkynes, which proceeds with high Z selectivity. Thus, this copper catalysis provides a useful method for the preparation of (Z)-alkenes from internal alkynes.

Synthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes

The first Ni-catalyzed Suzuki-Miyaura coupling of alkyl halides with alkenyl-(9-BBN) reagents is reported. Both primary and secondary alkyl halides including alkyl chlorides can be coupled. The coupling method can be combined with hydroboration of termina

1-tert-Butyl-1H-tetrazol-5-yl sulfones in the modified Julia olefination

The improved stability of metallated 1-tert-butyl-1H-tetrazol-5-yl sulfones enhances the scope and efficiency of the modified Julia olefination. 1-tert-Butyl-1H-tetrazol-5-yl sulfones further stabilised by benzylic or allylic conjugation give alkenes with