35505-99-8

Upstream product

• 4363-35-3 Dihydroxy-styryl-boran 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 16473-21-5 1-cyano-4-(fluoromethyl)benzene 
• 300-57-2 allylbenzene 
• 126747-14-6 4-cyanophenylboronic acid 
• 21040-45-9 Cinnamyl acetate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids

Allyl alcohols can be directly used for the palladium-catalyzed allylation of aryl- and vinyl-boronic acids without the aid of a base.

Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h

Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids

Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)-C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.

Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents

The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.

Palladium catalyzed Suzuki cross-coupling of benzyltrimethylammonium salts via C-N bond cleavage

A palladium catalyzed Suzuki cross-coupling for construction of Csp3-Csp2 bond via Csp3-N bond activation of benzyltrimethyl-ammonium salt is described. This reaction not only offered a highly efficient approach to diarylmethanes but also paved the way for the application of benzyltrimethylammonium salts in the palladium catalyzed cross coupling reactions.

Selective cross-coupling of organic halides with allylic acetates

A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids

Allylic alcohols can be used directly for the palladium(0)-catalyzed allylation of aryl- and alkenylboronic acids with a wide variety of functional groups. A triphenylphosphine-ligated palladium catalyst turns out to be most effective for the cross-coupling reaction and its low loading (less than 1 mol%) leads to formation of the coupling product in high yield. The Lewis acidity of the organoboron reagents and poor leaving ability (high basicity) of the hydroxyl group are essential for the cross-coupling reaction. The reaction process is atom-economical and environmentally benign, because it needs neither preparation of allyl halides and esters nor addition of stoichiometric amounts of a base. Furthermore, allylic alcohols containing another unsaturated carbon-carbon bond undergo arylative cyclization reactions leading to cyclopentane formation. The Royal Society of Chemistry.