89103-75-3

Upstream product

• 64-18-6 formic acid 
• 7693-90-5 (1R,2R)-1-bromo-1,2-diphenyl-propane 
• 141-53-7 sodium formate 
• 7693-90-5 (1S,2R)-1-bromo-1,2-diphenyl-propane 
• 58751-83-0 1,2-diphenylpropan-1-one 
• 7693-95-0 4-nitro-benzoic acid-((1S,2R)-1,2-diphenyl-propyl ester) 
• 17961-78-3 α-methylbenzyl(trimethyl)silane 
• 100-52-7 benzaldehyde 
• 98-85-1 1-Phenylethanol 
• 951-85-9 (S)-methyldesoxybenzoin 
• 34713-70-7 2-Phenylpropanal 
• 591-51-5 phenyllithium 
• 34278-65-4 4-bromo-benzenesulfonic acid-((S)-1-methyl-2,2-diphenyl-ethyl ester) 
• 127-09-3 sodium acetate 

Downstream Products

• 7693-90-5 (1R,2R)-1-bromo-1,2-diphenyl-propane 
• 7693-90-5 (1S,2R)-1-bromo-1,2-diphenyl-propane 
• 7693-88-1 (1R,2R)-1-chloro-1,2-diphenyl-propane 
• 7693-88-1 (1S,2R)-1-chloro-1,2-diphenyl-propane 
• 7693-94-9 toluene-4-sulfonic acid-((1R,2R)-1,2-diphenyl-propyl ester) 
• 58751-83-0 1,2-diphenylpropan-1-one 
• 18220-90-1 4-ethylbenzophenone 
• 7249-23-2 3-nitro-phthalic acid-1-((1RS,2RS)-1,2-diphenyl-propyl ester) 
• 5814-85-7 1,2-diphenylpropane 
• 7693-88-1 (1RS,2RS)-1-chloro-1,2-diphenyl-propane 
• 7693-90-5 (1RS,2RS)-1-bromo-1,2-diphenyl-propane 
• 7693-86-9 1,2-diphenylpropyl acetate 
• 67700-01-0 4-bromo-benzenesulfonic acid-((1RS,2RS)-1,2-diphenyl-propyl ester) 
• 7249-23-2 3-nitro-phthalic acid-1-((1RS,2SR)-1,2-diphenyl-propyl ester) 

Relevant academic research and scientific papers

Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes

Two methods are reported for the 1,2- and 1,1-arylboration of α-methyl vinyl arenes. In the case of 1,2-arylboration, the formation of a quaternary center occurred through a rare cross-coupling reaction of a tertiary organometallic complex. 1,1-Arylboration was enabled by catalyst optimization and occurred through a β-hydride elimination/reinsertion cascade. Enantioselective variants of both processes are presented as well as mechanistic investigations.

Nickel Catalyzed Intermolecular Carbonyl Addition of Aryl Halide

In this study, we develop a nickel-catalyzed carbonyl arylation reaction employing aldehydes with aryl and allyl halides. Various aryl, α,β-unsaturated aldehyde and aliphatic aldehydes can be converted into their corresponding secondary alcohols in moderate-to-high yields. In addition, we extended this approach to develop an asymmetric reductive coupling reaction that combines nickel salts with chiral bisoxazoline ligands to give secondary alcohols with moderate enantioselectivity.

Enantioselective Copper-Catalyzed Methylboration of Alkenes

An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis(pinacolato)diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, and challenging aliphatic olefins were smoothly transferred to the desired methylboration products with excellent diastereoselectivities (dr up to >99:1) and enantioselectivities (er up to 99:1). The utility of this process was demonstrated by the synthesis of naproxen and formal synthesis of two natural products.

Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids

A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.

Rhodium-catalysed tandem hydroformylation/arylation reaction with boronic acids

A new efficient multicatalytic process involving a single catalyst to promote tandem hydroformylation/arylation reactions is disclosed. The effect of the rhodium ligand was evaluated and the rhodium/triphenylphosphine catalytic system was selected to apply the methodology to different olefins and boronic acids. High yields (up to 89%) and good to excellent isomer ratios (up to 98:2) were achieved using aryl olefins as starting materials. This new methodology allows the preparation of secondary alcohols, from simple olefins, and paves the way for the synthesis of high-value products, namely vinylindole and anethole derivatives.

Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation

Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.

Role of free space and conformational control on photoproduct selectivity of optically pure α-alkyldeoxybenzoins within a water-soluble organic capsule

Optically pure α-alkyl deoxybenzoins resulting in products of Norrish Type I and Type II reactions upon excitation has been investigated within the octa acid (OA) capsule in water. The product distribution was different from that in an organic solvent and was also dependent on the length of the α-alkyl chain. Most importantly, a rearrangement product not formed in an organic solvent arising from the triplet radical pair generated by Norrish Type I reaction was formed, and its yield was dependent on the alkyl chain length. In an organic solvent, since the cage lifetime is shorter than the time required for intersystem crossing (ISC) of the triplet radical pair to the singlet radical pair the recombination with or without rearrangement of the primary radical pair (phenylacetyl and benzyl) does not occur. Recombination without rearrangement within the capsule as inferred from monitoring the racemization of the optically pure α-alkyl deoxybenzoins suggesting the capsule's stability for at least 10-8 s (the time required for ISC) is consistent with our previous photophysical studies that showed partial opening and closing of the capsule in the time range of microseconds.

Diastereoselective friedel-crafts alkylation of indoles with chiral α-phenyl benzylic cations. Asymmetric synthesis of anti-1,1,2- triarylalkanes

(Chemical Equation Presented) The reactions of chiral benzyl carbocations bearing α-phenyl substituents with N-sulfonylated indoles afford 1,1,2-triarylalkanes with antiselectivities. This outcome is a reversal of facial diastereoselectivity relative to B

Cadmium-mediated carbonyl benzylation in tap water

Zn/CdCl2 has been developed as a mediator in the benzylation of various aldehydes in tap water affording the corresponding alcohols in moderate to good yields. The addition of a catalytic amount of InCl3 increases the yield of benzylation product significantly. It can selectively mediate the benzylation of aldehydes in the presence of ketones. A mechanism involving the formation of a cation π-complex is proposed based on the experimental facts. Georg Thieme Verlag Stuttgart.

Lewis base-catalyzed addition of trialkylaluminum compounds to epoxides

A novel concept for catalytic epoxide alkylation has been developed. Lewis bases like phosphanes, arsanes, stibanes, and sulfides were found to catalyze the alkylation of symmetrical epoxides with trialkylaluminum compounds very effectively at a 5 mol % level. Cyclic as well as acyclic epoxides were readily alkylated in good yields. In reactions with terminal epoxides a significant enhancement of rate and/or regioselectivity was noted in the Lewis base-catalyzed process. Coordination of the Lewis base to the Lewis acidic aluminum reagent was proved by 27Al and 31p NMR spectroscopy and is proposed to form a more nucleophilic alkylating agent.