Alkyl nitrite-metal halide deamination reactions. 5. In situ generation of nitrosyl halides. Effective product control from nitrosyl chloride diazotization of primary aliphatic amines in N,N-dimethylformamide

1978 ◽  
Vol 43 (21) ◽  
pp. 4120-4125 ◽  
Author(s):  
Michael P. Doyle ◽  
Richard J. Bosch ◽  
Paul G. Seites
Keyword(s):  
Metal Halide ◽  
Aliphatic Amines ◽  
Nitrosyl Chloride ◽  
In Situ Generation ◽  
Effective Product ◽  
Alkyl Nitrite ◽  
Primary Aliphatic Amines ◽  
Product Control

A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 630-634 ◽  
Author(s):  
Min Zhang ◽  
Jinling Su ◽  
Yan Zhang ◽  
Mingren Chen ◽  
Weiming Li ◽  
...  
Keyword(s):  
Metal Halide ◽  
Regioselective Synthesis ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Copper Halide ◽  
Experimental Conditions ◽  
Heteroaromatic Compounds ◽  
Convenient Approach ◽  
In Situ Generation

A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX2 alone or with ZnX2) promoted halogenation with N-halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X+) by the coordination of copper or zinc with the N-halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

Highly diastereo- and enantioselective organocatalytic synthesis of trifluoromethylated erythritols based on the in situ generation of unstable trifluoroacetaldehyde

2021 ◽  
Author(s):  
Kazumasa Funabiki ◽  
Toshiya Gotoh ◽  
Ryunosuke Kani ◽  
Toshiyasu Inuzuka ◽  
Yasuhiro Kubota
Keyword(s):  
Trifluoromethyl Group ◽  
In Situ Generation

A highly diastereo- and enantioselective organocatalytic method to synthesise erythritols bearing a trifluoromethyl group has been investigated.

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>

Recent advances in Minisci-type reactions and applications in organic synthesis

2020 ◽  
Vol 24 ◽  
Author(s):  
Wengui Wang ◽  
Shoufeng Wang
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Organic Synthesis ◽  
Radical Reactivity ◽  
Atom Loss ◽  
Radical Generation ◽  
In Situ Generation ◽  
Thermal Cleavage ◽  
Synthetic Chemist

Abstract:: Minisci-type reactions have become widely known as reactions that involve the addition of carbon-centered radicals to basic heteroarenes followed by formal hydrogen atom loss. While the originally developed protocols for radical generation remain in active use today, in recent years by a new array of radical generation strategies allow use of a wider variety of radical precursors that often operate under milder and more benign conditions. New transformations based on free radical reactivity are now available to a synthetic chemist looking to utilize a Minisci-type reaction. Radical-generation methods based on photoredox catalysis and electrochemistry, which utilize thermal cleavage or the in situ generation of reactive radical precursors, have become popular approaches. Our review will cover the remarkably literature that has appeared on this topic in recent 5 years, from 2015-01 to 2020-01, in an attempt to provide guidance to the synthetic chemist, on both the challenges that have been overcome and applications in organic synthesis.

scholarly journals A residue-free approach to water disinfection using catalytic in situ generation of reactive oxygen species

2021 ◽  
Author(s):  
Thomas Richards ◽  
Jonathan H. Harrhy ◽  
Richard J. Lewis ◽  
Alexander G. R. Howe ◽  
Grzegorz M. Suldecki ◽  
...  
Keyword(s):  
Reactive Oxygen Species ◽  
Reactive Oxygen ◽  
Water Disinfection ◽  
Oxygen Species ◽  
In Situ Generation

In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones

2021 ◽  
Vol 23 (3) ◽  
pp. 1130-1134
Author(s):  
Haibo Mei ◽  
Li Wang ◽  
Romana Pajkert ◽  
Qian Wang ◽  
Jingcheng Xu ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
In Situ Generation
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