A Simplified Protocol for the ortho-Deuteration of Acidic Aromatic Compounds in D2O

2019 ◽  
Author(s):  
Alyssa Garreau ◽  
Hanyang Zhou ◽  
Michael Young
Keyword(s):  
Carboxylic Acid ◽  
Aromatic Compounds ◽  
Large Scale ◽  
Simplified Approach ◽  
Directing Group ◽  
Large Scale Synthesis

<div>Methods to catalytically introduce deuterium in synthetically useful yields ortho to a carboxylic acid directing group on arenes typically requires D2 or CD3CO2D, which makes using these approaches cost prohibitive for large scale synthesis (equipment and reagent costs respectively). Herein we present a simplified approach using catalytic RhIII and D2O as deuterium source, and show its application to H/D exchange on various acidic substrates.</div>

A Simplified Protocol for the ortho-Deuteration of Acidic Aromatic Compounds in D2O

2019 ◽  
Author(s):  
Alyssa Garreau ◽  
Hanyang Zhou ◽  
Michael Young
Keyword(s):  
Carboxylic Acid ◽  
Aromatic Compounds ◽  
Large Scale ◽  
Simplified Approach ◽  
Directing Group ◽  
Large Scale Synthesis

<div>Methods to catalytically introduce deuterium in synthetically useful yields ortho to a carboxylic acid directing group on arenes typically requires D2 or CD3CO2D, which makes using these approaches cost prohibitive for large scale synthesis (equipment and reagent costs respectively). Herein we present a simplified approach using catalytic RhIII and D2O as deuterium source, and show its application to H/D exchange on various acidic substrates.</div>

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Direct halogenation of organic compounds with halides using oxone in water — A green protocol

2009 ◽  
Vol 87 (12) ◽  
pp. 1675-1681 ◽  
Author(s):  
H. Firouzabadi ◽  
N. Iranpoor ◽  
S. Kazemi
Keyword(s):  
Carboxylic Acid ◽  
Organic Compounds ◽  
Aromatic Compounds ◽  
Large Scale ◽  
Unsaturated Alcohol ◽  
Green Protocol ◽  
Unsaturated Carboxylic Acid

Direct bromination and iodination of various aromatic compounds with NaBr and NaI using oxone (2KHSO5·KHSO4·K2SO4) in water was accomplished successfully in high-to-excellent yields. The main benefit of this protocol is the performance of the reactions in water in the presence of a harmless oxidant without the use of any organic co-solvents. Using NaBr and NaI as the safe sources of halogens is another advantage of the protocol. This method is easily applicable to the large-scale operations. We have also applied this method successfully for the iodocyclization of an unsaturated alcohol and an unsaturated carboxylic acid.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

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