1201694-46-3

Upstream product

• 26537-19-9 methyl 4-tert-butylbenzoate 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 

Relevant academic research and scientific papers

Formyl-selective deuteration of aldehydes with D2O: Via synergistic organic and photoredox catalysis

Formyl-selective deuteration of aldehydes is of high interest for labeling purposes and for optimizing properties of drug candidates. Herein, we report a mild general method for formyl-selective deuterium labeling of aldehydes with D2O, an inexpensive deuterium source, via a synergistic combination of light-driven, polyoxometalate-facilitated hydrogen atom transfer and thiol catalysis. This highly efficient, scalable reaction showed excellent deuterium incorporation, a broad substrate scope, and excellent functional group tolerance and selectivity and is therefore a practical method for late-stage modification of synthetic intermediates in medicinal chemistry and for generating libraries of deuterated compounds.

Reductive Deuteration of Aromatic Esters for the Synthesis of α,α-Dideuterio Benzyl Alcohols Using D 2O as Deuterium Source

α,α-Dideuterio benzyl alcohols are important building blocks for the synthesis of deuterium-labeled medicines and agrochemicals. We have developed the first general single-electron transfer reductive deuteration of readily commercially available aromatic

Visible-light-mediated deuteration of aldehydes with D2O via polarity-matched reversible hydrogen atom transfer

Hydrogen/deuterium exchange at the formyl groups of aldehydes is the most direct way to synthesize deuterated aldehydes, which are of interest for labeling studies and drug discovery. Herein, we report a mild, general protocol for visible-light-mediated m

Deoxygenative Deuteration of Carboxylic Acids with D2O

We report a general, practical, and scalable means of preparing deuterated aldehydes from aromatic and aliphatic carboxylic acids with D2O as an inexpensive deuterium source. The use of Ph3P as an O-atom transfer reagent can facilitate the deoxygenation of aromatic acids, while Ph2POEt is a better O-atom transfer reagent for aliphatic acids. The highly precise deoxygenation of complex carboxylic acids makes this protocol promising for late-stage deoxygenative deuteration of natural product derivatives and pharmaceutical compounds.

Method for preparing deuterated aldehyde from carboxylic acid using iridium complex as catalyst under irradiation of blue light

A method for preparing deuterated aldehyde from carboxylic acid using an iridium complex as a catalyst under the irradiation of blue light is as follows: aromatic carboxylic acid (ArCOOH) used as a raw material and triphenylphosphine used as a deoxidizing agent are irradiated by blue light in a solution of dichloromethane and heavy water, in the atmosphere of argon, under the condition of dipotassium phosphate used as alkali and using [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as a photocatalyst and thiophenol 2,4,6-triisopropylbenzenethiol as an organic small molecule catalyst to obtain a deuterated aromatic aldehyde compound; or aliphatic carboxylic acid (Alk-COOD) used as the raw material and diphenylethoxyphosphine used as a deoxidizing agent are irradiated by blue light in a solution of toluene, inthe atmosphere of argon and under the condition of 2,6-lutidine used as alkali to obtain a deuterated fatty aldehyde compound.

Method for preparing deuterated aldehyde compound by using halomethyl compound as raw material

The invention provides a method for preparing deuterated aldehyde compound by using halomethyl compound as a raw material. The method comprises the following steps that in solvent and D2O mixed liquidwith a pyridine compound, the halomethyl compound is added; reaction is performed at 0 to 100 DEG C; then, a nitrosobenzene type compound is added for continuous reaction; finally, reaction liquid issubjected to acidification to obtain a target product. The method has the advantages that the used raw materials are cheap and can be easily obtained; expensive reagents or heavy metal raw materialsare not needed; the reaction conditions are simple; the severe conditions such as high temperature are not needed; the cost of the preparation method is low; the operation is simple; the deuterated rate is high and can reach 97 percent; the target product can be easily purified; the yield is high and reaches up to 95 percent. The substrates used by the method have wide applicability; various deuterated aldehyde compounds can be prepared.

One-Pot Synthesis of Deuterated Aldehydes from Arylmethyl Halides

A facile, one-pot approach for synthesizing deuterated aldehydes from arylmethyl halides was developed using D2O as the deuterium source. The efficient process is realized by a sequence of formation, H/D exchange, and oxidation of pyridinium salt intermediates. The mild and air-compatible reaction conditions enable efficient synthesis of diverse deuterated aldehydes with high deuterium incorporation.

Computational and experimental structure-reactivity relationships: evidence for a side reaction in Alpine-Borane reductions of d-benzaldehydes

Extraordinary stereoselectivity, approaching 100%, has been reported in the reductions of d-benzaldehydes by B-isopinocampheyl-9-borabicyclo[3.3.1]nonane (Alpine-Borane). This is likely because of the extreme size disparity of groups on either side of the carbonyl. Here, we present a structure-reactivity study whereby the reductions of variably substituted d-benzaldehydes are explored using highly sensitive measures for enantiomeric excess and relative reactivity. These results are compared to the relative rates predicted from density functional calculations. The results indicate that 2,6-disubstitution adversely affects the stereoselectivity by means of a non-selective reduction via the dehydroboration product of Alpine-Borane, 9-borabicyclo[3.3.1]nonane.