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 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.

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.

Unusual orientation and reactivity of alkyl halides in water-soluble cavitands

2014 ◽  
Vol 5 (11) ◽  
pp. 4382-4387 ◽  
Author(s):  
Richard J. Hooley ◽  
Jesse V. Gavette ◽  
Magi Mettry ◽  
Dariush Ajami ◽  
Julius Rebek
Keyword(s):  
Alkyl Halides ◽  
Water Soluble

Reactions of the Binuclear Complexes [MIr(CO)3(Ph2PCH2PPh2)2] (M = Rh, Ir) with Alkyl Halides:  Dramatic Reactivity Differences as a Function of Metal Combination and Alkyl Halide

2000 ◽  
Vol 19 (5) ◽  
pp. 854-864 ◽  
Author(s):  
Jeffrey R. Torkelson ◽  
Okemona Oke ◽  
John Muritu ◽  
Robert McDonald ◽  
Martin Cowie
Keyword(s):  
Alkyl Halide ◽  
Alkyl Halides ◽  
Binuclear Complexes

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.

scholarly journals Direct C(sp2)–H alkylation of unactivated arenes enabled by photoinduced Pd catalysis

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Daeun Kim ◽  
Geun Seok Lee ◽  
Dongwook Kim ◽  
Soon Hyeok Hong
Keyword(s):  
Functional Group ◽  
Alkyl Halide ◽  
Alkyl Halides ◽  
Biologically Active ◽  
One Pot ◽  
Bond Forming ◽  
Alkyl Groups ◽  
Alkyl Bromides ◽  
Reaction Proceeds ◽  
Alkylation Reactions

AbstractDespite the fundamental importance of efficient and selective synthesis of widely useful alkylarenes, the direct catalytic C(sp2)–H alkylation of unactivated arenes with a readily available alkyl halide remains elusive. Here, we report the catalytic C(sp2)–H alkylation reactions of unactivated arenes with alkyl bromides via visible-light induced Pd catalysis. The reaction proceeds smoothly under mild conditions without any skeletal rearrangement of the alkyl groups. The direct syntheses of structurally diverse linear and branched alkylarenes, including the late-stage phenylation of biologically active molecules and an orthogonal one-pot sequential Pd-catalyzed C–C bond-forming reaction, are achieved with exclusive chemoselectivity and exceptional functional group tolerance. Comprehensive mechanistic investigations through a combination of experimental and computational methods reveal a distinguishable Pd(0)/Pd(I) redox catalytic cycle and the origin of the counter-intuitive reactivity differences among alkyl halides.

New synthetic reactions catalyzed by cobalt complexes

2006 ◽  
Vol 78 (2) ◽  
pp. 441-449 ◽  
Author(s):  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Palladium Catalysts ◽  
Alkyl Halide ◽  
Cobalt Complex ◽  
Cobalt Complexes ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Catalytic Activities ◽  
Cross Coupling Reactions ◽  
Synthetic Reactions

Without suffering from β-elimination, cobalt complexes allow cross-coupling reactions of alkyl halides with Grignard reagents. A combination of a cobalt complex and trimethylsilylmethyl Grignard reagent effects Mizoroki-Heck-type reaction of alkyl halide with styrene, which conventional palladium catalysts have never made possible. Cobalt exhibits intriguing catalytic activities on hydrophosphination and allylzincation of alkynes. Silylmethylcobalt reagent is a powerful tool for the synthesis of highly silylated ethenes.

Theoretical investigation on the binding of alkyl halides and cyclohexyl halides in water-soluble cavitands

2019 ◽  
Vol 728 ◽  
pp. 174-180
Author(s):  
Ioannis D. Petsalakis ◽  
Demeter Tzeli ◽  
Giannoula Theodorakopoulos ◽  
Julius Rebek
Keyword(s):  
Theoretical Investigation ◽  
Alkyl Halides ◽  
Water Soluble
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