220707-72-2

Upstream product

• 95306-90-4 4-(3-hydroxyprop-1-ynyl)acetophenone 
• 98-59-9 p-toluenesulfonyl chloride 
• 99-90-1 para-bromoacetophenone 
• 13329-40-3 4-Iodoacetophenone 

Downstream Products

• 109586-46-1 (E)-1-methoxy-4-(prop-1-en-1-yl)benzene 
• 586960-31-8 cyclopentadienyl(3-(4'-acetylphenyl)-2-propynyl)dicarbonyliron 

Relevant academic research and scientific papers

Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters

Iridium complexes modified by the chiral phosphine ligand PhanePhos catalyze the 2-propanol-mediated reductive coupling of diverse 1,1-disubstituted allenes 1a-1u with fluoral hydrate 2a to form CF3-substituted secondary alcohols 3a-3u that incorporate acyclic quaternary carbon-containing stereodiads. By exploiting concentration-dependent stereoselectivity effects related to the interconversion of kinetic (Z)- and thermodynamic (E)-σ-allyliridium isomers, adducts 3a-3u are formed with complete levels of branched regioselectivity and high levels of anti-diastereo- and enantioselectivity. The utility of this method for construction of CF3-oxetanes and CF3-azetidines is illustrated by the formation of 4a and 6a, respectively. Studies of the reaction mechanism aimed at illuminating the singular effectiveness of PhanePhos as a supporting ligand in this and related transformations have led to the identification of a chromatographically stable cyclometalated iridium-(R)-PhanePhos complex, Ir-PP-I, that is catalytically competent for allene-fluoral reductive coupling and previously reported transfer hydrogenative C-C couplings of dienes or CF3-allenes with methanol. Deuterium labeling studies, reaction progress kinetic analysis (RPKA) and computational studies corroborate a catalytic mechanism involving rapid allene hydrometalation followed by turnover-limiting carbonyl addition. A computationally determined stereochemical model shows that the ortho-CH2 group of the cyclometalated iridium-PhanePhos complex plays a key role in directing diastereo- and enantioselectivity. The collective data provide key insights into the structural-interactional features of allyliridium complexes required to enforce nucleophilic character, which should inform the design of related cyclometalated catalysts for umpoled allylation.

Co2(CO)8-mediated Selective Reductions of Propargyl Alcohol Derivatives to Alkenes

In the presence of Co2(CO)8 and additives, propargyl alcohol derivatives could be reduced to alkenes in moderate to good yield. The selectivity of this reaction could be controlled by adding different additives: with H2O as the additive, the major configuration of product is Z-alkene; with CF3COOH as the additive, the major configuration of product is E-alkene.

Preparation of substituted transition-metal (η1-propargyl complexes and their [3+2] cycloaddition reactions with sulfur dioxide and disulfur monoxide. Transition-metal - Carbon bond cleaving reactions of the cycloadducts which yield oxathiolene oxides and dithiolene oxides

The preparations of several new cyclopentadienyl iron dicarbonyl η1-2-alkynyl complexes are reported. Their [3+2] cycloaddition reactions with sulfur dioxide and disulfur monoxide yielded transition-metal substituted 1,2-oxathiolene-2-oxides and 1,2-dithiolene-1-oxides, respectively. The transition-metal was cleaved from the oxathiolene-oxide and dithiolene-oxide containing complexes to produce new sulfur heterocycles.