59059-42-6

Upstream product

• 54887-24-0 2-butylbenzoyl chloride 
• 542-69-8 1-iodo-butane 
• 100-52-7 benzaldehyde 
• 107-08-4 1-iodo-propane 
• 529-20-4 2-methylphenyl aldehyde 
• 115765-22-5 (E)-N-(2-chlorobenzylidene)cyclohexanamine 
• 4426-47-5 butylboronic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 57598-33-1 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 57629-47-7 2-(2-Butylphenyl)-4,4-dimethyl-2-oxazoline 
• 54887-23-9 2-butylbenzoic acid 
• 1461-25-2 tetra-n-butyltin(IV) 
• 109-72-8 n-butyllithium 
• 109-65-9 1-bromo-butane 

Downstream Products

• 34139-47-4 2-(n-Butyl)cyclohexylmethylbenzol 
• 34139-46-3 2-n-Butylphenyl-diazomethan 
• 112562-04-6 2-(2-Butyl-phenyl)-thiazolidine-3-carbothioic acid methylamide 
• 20983-15-7 o-crotyltoluene 
• 1268267-75-9 5-(2-butylbenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant academic research and scientific papers

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

Intramolecular C-H activation through gold(I)-catalyzed reaction of iodoalkynes

The cycloisomerization reaction of 1-(iodoethynyl)-2-(1-methoxyalkyl)arenes and related 2-alkyl-substituted derivatives gives the corresponding 3-iodo-1-substituted-1H-indene under the catalytic influence of IPrAuNTf2 [IPr = 1,3-bis(2,6-diisopropyl)phenylimidazol-2-ylidene; NTf2 = bis(trifluoromethanesulfonyl)imidate]. The reaction takes place in 1,2-dichloroethane at 80°C, and the addition of ttbp (2,4,6-tritert-butylpyrimidine) is beneficial to accomplish this new transformation in high yield. The overall reaction implies initial assembly of an intermediate gold vinylidene upon alkyne activation by gold(I) and a 1,2-iodine-shift. Deuterium labeling and crossover experiments, the magnitude of the recorded kinetic primary isotopic effect, and the results obtained from the reaction of selected stereochemical probes strongly provide support for concerted insertion of the benzylic C-H bond into gold vinylidene as the step responsible for the formation of the new carbon-carbon bond.

Water-stabilized three- and four-atom palladium clusters as highly active catalytic species in ligand-free C-C cross-coupling reactions

Elite cliques: Palladium clusters with three and four atoms were found to be the catalytically active species for ligand-free palladium-catalyzed C-C bond-forming reactions (see picture). These palladium cluster species could be stabilized in water and stored for long periods of time for use on demand with no loss of activity. High yields of products and turnover frequencies (TOFs) of up to 105 h-1 were observed. Copyright

Expeditious construction of a carbobicyclic skeleton via sp3-C-H functionalization: Hydride shift from an aliphatic tertiary position in an internal redox process

Described herein is the first example of an aliphatic, nonbenzylic hydride shift/cyclization sequence that contains two types of novel sp3-C-H functionalization: (1) construction of a tetraline skeleton via [1,5]-hydride shift/cyclization and (2) [1,6]-hydride shift/cyclization to form a five-membered ring (indane derivatives).

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids

Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.

Manganese-catalyzed substitution of activated aryl halides (X = Cl, Br and F) and aryl ethers by organomagnesium reagents

In the presence of manganese chloride (10%), Grignard reagents readily react in THF with aryl bromides, chlorides and even fluorides, as well as aryl methyl ethers bearing in the ortho- or para-position an electron withdrawing activating group (CN, CH=NR, oxazoline). Aryl and N- or S- alkylmagnesium halides have been used successfully. The reaction is performed under mild conditions (0 °C to room temperature, 30 minutes to 24 hours) and leads to cross-coupling products in good yields.

Nucleophilic aromatic substitution on aromatic aldimines

Ortho-methoxy-substituted benzaldimines derived from 3-amino-2,4-dimethylpentane undergo efficient nucleophilic aromatic substitution with typical organolithium reagents. The aldimine products can be hydrolyzed under mild conditions to provide ortho-alkyl or ortho-phenyl benzaldehyde derivatives.

Transition Metal Catalyzed Grignard Cross-Coupling to Ortho-Halogenated Aryl Imines. An Efficient Synthesis of Ortho-Substituted Aryl Aldehydes

N-(o-Halogenated benzylidene)cyclohexylamines 2 were successfully reacted with reducing and nonreducing Grignard reagents in a transition metal catalyzed cross-coupling reaction resulting in an efficient single-step synthesis of ortho-substituted benzaldehydes after acidic workup.The dihalogenated benzylidene amines reacted regioselectively at the amine-activated ortho position to yield ortho-substituted halogenated benzaldehydes.

PALLADIUM-MEDIATED 2,6-DIALKYLATION OF N-BENZILIDINE IMINES: PREPARATION OF 2,6-DIALKYLBENZALDEHYDES

Treatment of di-μ-trifluoroacetatobisdipalladium with two equivalents of primary alkyl iodides and subsequent hydrolysis provides an efficient route to 2,6-disubstituted benzaldehydes.