4-Aminophenyldiphenylphosphinite (APDPP), a new heterogeneous and acid scavenger phosphinite — Conversion of alcohols, trimethylsilyl, and tetrahydropyranyl ethers to alkyl halides with halogens or N-halosuccinimides

2006 ◽  
Vol 84 (7) ◽  
pp. 1006-1012 ◽  
Author(s):  
Nasser Iranpoor ◽  
Habib Firouzabadi ◽  
Mohammad Gholinejad
Keyword(s):  
Trimethylsilyl Ether ◽  
Alkyl Halide ◽  
Alkyl Halides ◽  
Amino Group ◽  
Efficient Conversion ◽  
Trimethylsilyl Ethers ◽  
Simple Filtration ◽  
Tetrahydropyranyl Ether ◽  
Conversion Of Alcohols

A new heterogeneous phosphinite, 4-aminophenyldiphenylphosphinite (APDPP), is prepared and used for the efficient conversion of alcohols, trimethylsilyl ethers, and tetrahydropyranyl ethers to their corresponding bromides, iodides, and chlorides in the presence of molecular halogens or N-halosuccinimides. The amino group in this phosphinite acts as an acid scavenger and removes the produced acid. A simple filtration easily removes the phosphinate by-product.Key words: 4-aminophenyldiphenylphosphinite, alcohol, trimethylsilyl ether, tetrahydropyranyl ether, alkyl halide.

Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides

2017 ◽  
Vol 15 (45) ◽  
pp. 9638-9642 ◽  
Author(s):  
Yaqi Yang ◽  
Zihang Ye ◽  
Xu Zhang ◽  
Yipeng Zhou ◽  
Xiantao Ma ◽  
...  
Keyword(s):  
Transition Metal ◽  
Alkyl Halide ◽  
Alkyl Halides ◽  
Alkylation Reaction

Alcohols can be efficiently converted into thioethers by a transition metal- and base-free alkyl halide-catalyzed S-alkylation reaction with thiols or disulfides.

Binding of alkyl halides in water-soluble cavitands with urea rims

2018 ◽  
Vol 42 (12) ◽  
pp. 9945-9948 ◽  
Author(s):  
Yang Yu ◽  
Yong-Sheng Li ◽  
Julius Rebek
Keyword(s):  
Alkyl Halide ◽  
Alkyl Halides ◽  
Water Soluble

Alkyl halide guests in cavitands move rapidly and maintain halide to contact with the aryl surfaces of the host.

Efficient Conversion of Alkyl Halides to Aldehydes Using Pyrazinylsulfinyl Group

Heterocycles ◽  
1988 ◽  
Vol 27 (7) ◽  
pp. 1643 ◽  
Author(s):  
Akihiro Ohta ◽  
Makoto Shimazaki ◽  
Takako Nakanishi ◽  
Minoru Mochizuki
Keyword(s):  
Alkyl Halides ◽  
Efficient Conversion

scholarly journals One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

2013 ◽  
Vol 9 ◽  
pp. 2378-2386 ◽  
Author(s):  
Diego Carnaroglio ◽  
Katia Martina ◽  
Giovanni Palmisano ◽  
Andrea Penoni ◽  
Claudia Domini ◽  
...  
Keyword(s):  
Wittig Reaction ◽  
Scale Up ◽  
Alkyl Halides ◽  
Secondary Amines ◽  
Nucleophilic Substitutions ◽  
One Pot ◽  
Urea Derivatives ◽  
Step Process ◽  
Microwave Assisted ◽  
Simple Filtration

A fast and efficient protocol for the synthesis of N,N'-disubstituted urea derivatives from alkyl halides and primary or secondary amines has been developed. The synthetic pathway combines nucleophilic substitutions and a Staudinger–aza-Wittig reaction in the presence of polymer-bound diphenylphosphine under 14 bar of CO2 pressure and has been performed in a one-pot two-step process. The protocol has been optimized under microwave irradiation and the scale-up experiment has been conducted under conventional conditions in a Parr reactor. The final compounds were isolated after simple filtration in almost quantitative overall yields which makes this procedure facile and rapid to execute.

scholarly journals Electrochemically Driven Cross-Electrophile Coupling of Alkyl Halides

2021 ◽  
Author(s):  
Song Lin ◽  
Wen Zhang ◽  
Lingxiang Lu ◽  
Wendy Zhang ◽  
Jose Mondragon ◽  
...  
Keyword(s):  
High Selectivity ◽  
Alkyl Halide ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Critical Problem ◽  
Metal Free ◽  
Drug Candidates ◽  
Synthetic Accessibility ◽  
Alkyl Electrophiles ◽  
Direct Cross

Recent research in medicinal chemistry suggests a correlation between an increase in the fraction of sp3 carbons in drug candidates with their improved success rate in clinical trials. As such, the development of robust and selective methods for the construction of C(sp3)-C(sp3) bonds remains a critical problem in modern organic chemistry. Owing to the broad availability and synthetic accessibility of alkyl halides, their direct cross coupling—commonly known as cross-electrophile coupling (XEC)—provides a promising route toward this objective. However, achieving high selectivity in C(sp3)-C(sp3) XEC remains a largely unmet challenge. Herein, we employ electrochemistry to achieve the differential activation of alkyl halides by exploiting their disparate electronic and steric properties. Specifically, the selective cathodic reduction of a more substituted alkyl halide gives rise to a carbanion, which undergoes preferential coupling with a less substituted alkyl halide via bimolecular nucleophilic substitution (SN2) to forge a new C–C bond. This transition-metal free protocol enables the efficient XEC of a variety of functionalized and unactivated alkyl electrophiles and exhibits substantially improved chemoselectivity versus existing methodologies.

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