84920-36-5

Upstream product

• 627-09-8 Propargyl acetate 
• 2550-26-7 4-Phenyl-2-butanone 
• 106-96-7 propargyl bromide 
• 1314099-29-0 B-allenyl-1,3,2-dioxaborolane 
• 624-65-7 2-propynyl chloride 
• 108521-65-9 prop-2-yn-1-yl 4-methylbenzoate 
• 1020850-77-4 trifluoromethanesulfonic acid 2-methyl-6-oxo-2-phenethyl-3,6-dihydro-2H-pyran-4-yl ester 
• 75-16-1 methylmagnesium bromide 
• 57186-58-0 2-allenyl-5,5-dimethyl-1,3,2-dioxaborinane 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

CpTiCl2, an Improved Titanocene(III) Catalyst in Organic Synthesis

Preparation, EPR analysis, and advantages in green organic chemistry of CpTiCl2, an improved single-electron transfer catalyst, are reported. Under mild conditions, this organometallic complex provides excellent yields of homoallylic and homopropargylic alcohols in Barbier-type allylation and propargylation reactions. Moreover, in the presence of a bidentate BOX ligand, Barbier-type cyclization reactions catalyzed by CpTiCl2 can be carried out in an enantioselective manner.

Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate

Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.

Zinc-catalyzed allenylations of aldehydes and ketones

The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc int

Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols

Chiral biphenols catalyze the enantioselective asymmetric propargylation of ketones using allenylboronates. The reaction uses 10 mol % of 3,3′-Br2-BINOL as the catalyst and allenyldioxoborolane as the nucleophile, in the absence of solvent, and

Toluates: unexpectedly versatile reagents

The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted.

Ring opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols

Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 → 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols. Copyright

Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium

Reactions of organogallium reagents generated from propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields.

Palladium-Catalyzed Reaction of Propargylic Acetates with Carbonyl Compounds by SmI2

Reductive addition of propargylic acetates to carbonyl compounds proceeded smoothly at room temperature by using SmI2 and a catalytic amount of Pd(PPh3)4 to give the corresponding acetylenic and/or allenic alcohols with appreciable seletivity.The method i