42007-03-4

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 42006-91-7 4-bromobenzyl-α,α-d₂ alcohol 
• 589-17-3 p-bromobenzyl chloride 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 586-76-5 4-Bromobenzoic acid 
• 106-37-6 1.4-dibromobenzene 
• 4472-41-7 d₇-N,N-dimethylformamide 
• 51044-13-4 4-bromobenzyl triphenylphosphonium bromide 

Downstream Products

• 127986-91-8 (R)-p-bromobenzyl-1-d alcohol 
• 1028938-90-0 C₁₁H₁₀⁽²⁾HBr 
• 42006-91-7 4-bromobenzyl-α,α-d₂ alcohol 

Relevant academic research and scientific papers

Laser Flash Photolysis Study of the Effects of Substituents, Solvents, and Quenchers on the Triplet State of Benzaldehydes. H/D Exchange Following Quenching by D2O

The deactivation pathways of the lowest triplet state of benzaldehyde (BA), a series of substituted derivatives (OCH3, CH3, F, Cl, Br, CHO, and CN), and some related aromatic aldehydes were examined at room temperature by laser flash photolysis in several

Programmable iodization/deuterolysis sequences of phosphonium ylides to access deuterated benzyl iodides and aromatic aldehydes

Herein, a tunable iodization/deuterolysis protocol for phosphonium ylides by employing D2O as the deuterium source was designed. Notably, this process could be manipulated by tuning the base, thus leading to two valuable deuterated building blocks - benzyl iodides and aromatic aldehydes with broad substrate scope, good functional group compatibility and excellent deuteration degree. Concise syntheses of a series of deuterated drug analogues have been achieved based on the developed deuteration reaction platform.

VISIBLE-LIGHT MEDIATED ORGANOPHOTOREDOX CATALYTIC DEUTERATION OF AROMATIC AND ALIPHATIC ALDEHYDES

Described are methods for preparing a deuterated aldehyde using with a photocatalyst and a hydrogen atom transfer agent in a H2O free solvent comprising D2O and an organic solvent under an inert gas. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions.

SYNTHESIS OF DEUTERATED ALDEHYDES

Described are methods for preparing a deuterated aldehyde using N-heterocyclic carbene catalysts in a solvent comprising D2O. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions without functionality manipulation.

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

Selective oxidation of alcohol-d1to aldehyde-d1using MnO2

The selective oxidation of alcohol-d1to prepare aldehyde-d1was newly developed by means of NaBD4reduction/activated MnO2oxidation. Various aldehyde-d1derivatives including aromatic and unsaturated ald

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.

Visible light driven deuteration of formyl C-H and hydridic C(sp3)-H bonds in feedstock chemicals and pharmaceutical molecules

Deuterium labelled compounds are of significant importance in chemical mechanism investigations, mass spectrometric studies, diagnoses of drug metabolisms, and pharmaceutical discovery. Herein, we report an efficient hydrogen deuterium exchange reaction u

Deuteration of Formyl Groups via a Catalytic Radical H/D Exchange Approach

H/D exchange at formyl groups represents the straightforward approach to C-1 deuterated aldehydes. This transformation has been recently realized by transition metal and NHC carbene catalysis. Mechanistically, all of these processes involve an ionic pathway. Herein, we report a distinct photoredox catalytic, visible light mediated neutral radical approach. Selective control of highly reactive acyl radical in the energy barrier surmountable, reversible reaction enables driving the formation of deuterated products when an excess of D2O is employed. The power of the H/D exchange process has been demonstrated for not only aromatic aldehydes but also aliphatic substrates, which have been difficult in transitional metal catalyzed H/D exchange reactions, and for selective late-stage deuterium incorporation into complex structures with uniformly high deuteration level (>90%).

N-Heterocyclic Carbene Catalyzed Deuteration of Aldehydes in D 2 O

An N-heterocyclic carbene (NHC)-catalyzed direct deuteration of aldehydes in a mixed solvent of deuterium oxide (D 2 O) and cyclopentyl methyl ether was established. The present deuteration is possibly initiated by the formation of a Breslow intermediate from the aldehyde and the NHC, with subsequent trapping by D 2 O providing the monodeuterated aldehyde.