95307-64-5

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 95307-62-3 α-(4-benzyloxyphenyl)-α-morpholinoacetonitrile 
• 95307-63-4 α-(4-benzyloxyphenyl)-α-morpholino<α-2H>acetonitrile 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 50816-33-6 4-benzyloxybenzaldehyde 

Downstream Products

• 95307-65-6 4-hydroxybenzaldehyde 
• 1426955-68-1 (R)-(-)-4-triisopropyloxybenzyl-α-d chloride 
• 1426955-69-2 (2S,3S)-N-benzoyl-O-triisopropylsilyl-[3-²H,¹⁵N]-tyrosine (-)-8-phenylmenthyl ester 
• 1426955-71-6 (2S,3S)-N-benzoyl-[3-²H,¹⁵N]-tyrosine (-)-8-phenylmenthyl ester 
• 1426955-73-8 (2S,3S)-[3-²H,¹⁵N]-tyrosine hydrochloride 
• 1426955-67-0 4-triisopropylsilyloxybenzaldehyde-α-d 
• 1480252-38-7 C₁₆H₁₀⁽²⁾HNO₃ 
• 1448510-81-3 (R)-4'-O,3-N-di(ethoxycarbonyl)-β-tyrosine ethyl ester 
• 1448510-84-6 C₁₆H₂₀⁽²⁾HNO₇ 
• 1448510-72-2 (Z)-2-benzamido-[3-²H]-3-(4-hydroxyphenyl)acrylic acid 
• 34100-65-7 (2S,3R)-[2,3-²H]-α-tyrosine 
• 1147299-53-3 4-((3-fluorophenyl)methoxy-d2)benzaldehyde-d1 
• 95307-66-7 2',4,4'-trihydroxy<β,3,5-2H3>chalcone 
• 1026151-43-8 4-[7,9,9-⁽²⁾H₃]coumaryl alcohol 

Relevant academic research and scientific papers

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.

Rerouting the Organocatalytic Benzoin Reaction toward Aldehyde Deuteration

Reactive intermediates are key to halting and promoting chemical transformations; however, due to their elusive nature, they are not straightforwardly harnessed for reaction design. Herein, we describe studies aimed at stabilizing reactive intermediates in the N-heterocyclic carbene (NHC) catalytic cycle, which enabled the full shutdown of the known benzoin coupling pathway, while rerouting its intermediates toward deuteration. The reversible nature of NHC catalysis and the selective stabilization of reaction intermediates facilitated clean hydrogen-deuterium exchange reactions of aromatic aldehydes by D2O, even for challenging electron-withdrawing substrates. In several cases, the addition of catalytic amounts of phenyl boronic acid was used to further stabilize highly reactive intermediates and mitigate the formation of benzoin coupling byproducts. The mechanistic understanding at the foundation of this work resulted in unprecedented mild conditions with base and catalyst loadings as low as 0.1 mol %, and a scalable deuteration reaction applicable to a broad substrate scope with outstanding functional group tolerance. More importantly, adopting this approach enabled the construction of a guideline for identifying the appropriate catalyst and conditions for different substrates. Experimental studies combined with machine learning and computational methods shed light on the nontrivial mechanistic underpinnings of this reaction.

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%).

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

Catalytic Deuteration of Aldehydes with D 2 O

A procedure is presented that enables the direct deuteration of the formyl C-H bond of aldehydes using D 2 O as the deuterium source and commercially available RuHCl(CO)(PPh 3) 3 as the catalyst. Up to 84% deuterium incorp

Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: Synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine

Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride. Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position. Copyright

Isoflavonoid Biosynthesis: Concerning the Aryl Migration

Feeding experiments with 13C- or 2H-labelled precursors in CuCl2-treated red clover (Trifolium pratense) seedings have demonstrated that the isoflavone formononetin (6) and the pterocarpan phytoalexins medicarpin (10) and maackiain (11) are biosynthesized