40715-68-2

Upstream product

• 35856-81-6 1-methoxy-4-(3-phenyl-1-propen-1-yl)benzene 
• 35856-80-5 4-(3-phenylallyl)anisole 
• 98-86-2 acetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 637-59-2 1-Bromo-3-phenylpropane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 768-56-9 4-Phenylbut-1-ene 
• 591-50-4 iodobenzene 
• 104-46-1 anethole 
• 90878-19-6 phenethylmagnesium chloride 
• 824-94-2 p-methoxybenzyl chloride 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 959-23-9 4'-methoxychalcone 

Relevant academic research and scientific papers

Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides

Alkyl chlorides and aryl chlorides are among the most abundant and stable carbon electrophiles. Although their coupling with carbon nucleophiles is well developed, the cross-electrophile coupling of aryl chlorides with alkyl chlorides has remained a chall

Substituted Hantzsch Esters as Versatile Radical Reservoirs in Photoredox Reactions

Substituted Hantzsch esters can act as radical reservoirs in photoredox reactions, steadily releasing a carbon radical and a hydrogen atom radical in the absence of an additional electron acceptor. We propose that radical release by substituted Hantzsch esters occurs via a mechanism involving an internal redox cycle. Cinnamidecinnamides, styrenes, α,β-unsaturated acids, and diarylethenes could be alkylated smoothly with these reagents. (Figure presented.).

Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

Switchable Selectivity in the Pd-Catalyzed Alkylative Cross-Coupling of Esters

The Pd-catalyzed cross-coupling of phenyl esters and alkyl boranes is disclosed. Two reaction modes are rendered accessible in a selective fashion by interchange of the catalyst. With a Pd-NHC system, alkyl ketones can be prepared in good yields via a Suzuki-Miyaura reaction proceeding by activation of the C(acyl)-O bond. Use of a Pd-dcype catalyst enables alkylated arenes to be synthesized by a modified pathway with extrusion of CO. Applications of this divergent coupling strategy and the origin of the switchable selectivity are discussed.

B-Alkyl sp3-sp2 Suzuki-Miyaura Couplings under Mild Aqueous Micellar Conditions

Use of B-sp3-alkyl reagents for Suzuki-Miyaura couplings under aqueous micellar catalysis conditions is reported. Studies as to substrate scope, use in a four-step one-pot sequence, and reaction medium recycling exemplify the synthetic utility of this technology. OBBD (B-alkyl-9-oxa-10-borabicyclo[3.3.2]decane) derivatives are easily made and utilized for couplings under mild conditions. Comparisons were also made between OBBD and 9-BBN (B-alkyl-9-borabicyclo[3.3.1]nonane) derivatives as reaction partners.

Modular radical cross-coupling with sulfones enables access to sp3-rich (fluoro)alkylated scaffolds

Cross-coupling chemistry is widely applied to carbon-carbon bond formation in the synthesis of medicines, agrochemicals, and other functional materials. Recently, single-electron-induced variants of this reaction class have proven particularly useful in the formation of C(sp2)-C(sp3) linkages, although certain compound classes have remained a challenge. Here, we report the use of sulfones to activate the alkyl coupling partner in nickel-catalyzed radical cross-coupling with aryl zinc reagents. This method's tolerance of fluoroalkyl substituents proved particularly advantageous for the streamlined preparation of pharmaceutically oriented fluorinated scaffolds that previously required multiple steps, toxic reagents, and nonmodular retrosynthetic blueprints. Five specific sulfone reagents facilitate the rapid assembly of a vast set of compounds, many of which contain challenging fluorination patterns.

Ligand-Controlled Chemoselective C(acyl)-O Bond vs C(aryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings

A ligand-controlled and site-selective nickel catalyzed Suzuki-Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed. This methodology provides a facile route for C(sp2)-C(sp3) bond formation in a straightforward fashion by successful suppression of the undesired β-hydride elimination process. By simply switching the phosphorus ligand, the ester substrates are converted into the alkylated arenes and ketone products, respectively. The utility of this newly developed protocol was demonstrated by its wide substrate scope, broad functional group tolerance and application in the synthesis of key intermediates for the synthesis of bioactive compounds. DFT studies on the oxidative addition step helped rationalizing this intriguing reaction chemoselectivity: whereas nickel complexes with bidentate ligands favor the C(aryl)-C bond cleavage in the oxidative addition step leading to the alkylated product via a decarbonylative process, nickel complexes with monodentate phosphorus ligands favor activation of the C(acyl)-O bond, which later generates the ketone product.

Iron-Catalyzed C(sp 2)-C(sp 3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides

An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C-C bond-forming reactions.

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters

A novel Suzuki-Miyaura protocol is described that enables the exhaustive alkylation of polychlorinated pyridines. This method facilitates a formal synthesis of normuscopyridine and the rapid assembly of a dumbbell shaped portion of a [2]rotaxane.