100765-50-2

Upstream product

• 693-04-9 butyl magnesium bromide 
• 104-82-5 4-Methylbenzyl chloride 
• 64-17-5 ethanol 
• 3391-86-4 1-octen-3-ol 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 624-31-7 4-tolyl iodide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 106-38-7 para-bromotoluene 

Relevant academic research and scientific papers

Generation of metalloenamines by carbon-carbon bond formation: Ring opening reactions of 2-methyleneaziridines with organometallic reagents

Ring opening of 2-methyleneaziridines with Grignard reagents in the presence of CuI yields metalloenamines in a regiospecific fashion which can be further reacted with electrophiles to produce functionalised ketones via a one-pot process.

Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts

Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.

Palladium-Catalyzed Desulfitative Oxidative Coupling between Arenesulfinic Acid Salts and Allylic Alcohols: A Strategy for the Selective Construction of β-Aryl Ketones and Aldehydes

An efficient palladium-catalyzed desulfitative oxidative coupling of sodium arylsulfinites for highly region-selective Heck-type reaction of allylic alcohols has been developed. The compatibility of the functionalities of -I, -Br, and -F would explore further postfunctionalization of the C-X bonds. This method provides a new and straightforward protocol for the synthesis of β-aryl ketones and aldehydes. The deuterium labeling experiments indicated that this transformation may proceed via a [1, 2-H] shift process.

Aerobic oxidative coupling between carbon nucleophiles and allylic alcohols: A strategy to construct β-(hetero)aryl ketones and aldehydes through hydrogen migration

Wacker heck of a reaction: A highly efficient PdII-catalyzed intermolecular oxidative-coupling reaction is reported, inspired by the fundamental Heck and Wacker processes. The (hetero)aryl-PdX species, originating from C-H activation step or desulfonyl hydrazides, coupled with allylic alcohols by using oxygen as the sole oxidant (see scheme). Copyright

Palladium-catalyzed Heck arylations of allyl alcohols in ionic liquids: Remarkable base effect on the selectivity

Pd-catalyzed Heck arylation of allyl alcohols in tetraalkylammonium ionic liquids (ILs) can be made highly selective toward the formation of either aromatic carbonyl compounds or aromatic conjugated alcohols by carefully choosing both the IL and the base.

Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols

Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.