100789-95-5

Upstream product

• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 17988-20-4 (4-methoxy-benzyl)-trimethyl-silane 
• 2419-67-2 (E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one 
• 507-19-7 t-butyl bromide 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 

Downstream Products

• 1033774-86-5 2-bromo-1-(4-methoxyphenyl)-4,4-dimethylpentan-3-one 

Relevant academic research and scientific papers

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates

Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.

Ni-catalyzed reductive coupling of alkyl acids with unactivated tertiary alkyl and glycosyl halides

This work highlights Ni-catalyzed reductive coupling of alkyl acids with alkyl halides, particularly sterically hindered unactivated tertiary alkyl bromides for the production of all carbon quaternary ketones. The reductive strategy is applicable to α-selective synthesis of saturated, fully oxygenated C-acyl glycosides through easy manipulations of the readily available sugar bromides and alkyl acids, avoiding otherwise difficult multistep conversions. Initial mechanistic studies suggest that a radical chain mechanism (cycle B, Scheme 1) may be plausible, wherein MgCl2 promotes the reduction of NiII complexes.

Selective Cross Coupling via Oxovanadium(V)-Induced Oxidative Desilylation of Benzylic Silanes

Benzylic silanes bearing an electron-donating group at the ortho- or para-position underwent the oxovanadium(V)-induced one-electron oxidative desilylation due to low ionization potential, which was applied to the intermolecular regioselective coupling with allylic silanes or silyl enol ether.