1556-18-9

Usage

Uses

Iodocyclopentane may be used in the synthesis of 4-chloro-3′-((2-cyclopentyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-6- yloxy)methyl)biphenyl-3-carboxylic acid and N-(3-methoxyphenethyl)cyclopentanamine.

InChI:InChI=1/C8H7NOS/c1-10-8-4-2-3-7(5-8)9-6-11/h2-5H,1H3

Upstream product

• 137-43-9 Cyclopentyl bromide 
• 96-41-3 Cyclopentanol 
• 4415-82-1 cyclobutanemethanol 
• 3558-06-3 cyclopentyl tosylate 
• 285-67-6 Cyclopentene oxide 
• 287-92-3 Cyclopentane 
• 7553-56-2 iodine 
• 84559-49-9 cyclopentylpentaaquochromium(III) 
• 10034-85-2 hydrogen iodide 
• 3889-74-5 cyclopentyl radical 
• 142-29-0 cyclopentene 

Downstream Products

• 18928-91-1 diethyl 2-cyclopentylmalonate 
• 4254-02-8 cyclopentanecarbonitrile 
• 287-92-3 Cyclopentane 
• 142-29-0 cyclopentene 
• 2562-38-1 nitrocyclopentane 
• 5623-81-4 2-cyclopentylacetaldehyde 
• 2040-95-1 n-butylcyclopentane 
• 137-43-9 Cyclopentyl bromide 
• 3753-59-1 rac-cyclopentyl(phenyl)acetonitrile 
• 74-90-8 hydrogen cyanide 
• 116530-81-5 1-methyl-1-nitro-cyclobutane 
• 438207-21-7 3-cyclopentyl-N-(4-methyl-benzyl)-propionamide 

Relevant academic research and scientific papers

The first efficient iodination of unactivated aliphatic hydrocarbons

No heavy metals, no enzymes, and a simple protocol: the direct iodination of aliphatic hydrocarbons, which has not been possible to date, can now be carried out in multiphase systems [see for example Eq. (l)]. In situ generated tetraiodomethane serves as a key intermediate in this selective radical chain reaction initiated by a single electron transfer. This room-temperature, efficient transformation is highly regioselective, easy to work-up, and hence widely applicable.

First examples of superelectrophile initiated iodination of alkanes and cycloalkanes

Direct iodination of alkanes and cycloalkanes in the presence of superelectrophiles has been accomplished for the first time. The reactions of saturated hydrocarbons with I2 in the presence of CCl4·2AlI3 at -20°C afforded monoiodides in good yields and selectivities.

A CONVENIENT METHOD FOR THE ADDITION OF HI TO UNSATURATED HYDROCARBONS USING I2 ON Al2O3

Iodine reacts, under mild conditions, with hydroxyl groups on the surface of alumina to form HI which readily adds to unsaturated hydrocarbons to form alkyl and vinyl iodides.

Photoinduced Palladium-Catalyzed Dicarbofunctionalization of Terminal Alkynes

Herein, a conceptually distinct approach was developed that allowed for the dicarbofunctionalization of alkynes at room temperature using simple, bench-stable alkyl iodides and a second molecule of alkyne as coupling partner. Specifically, the photochemical activation of palladium complexes enabled this strategic dicarbofunctionalization via addition of alkyl radicals from secondary and tertiary alkyl iodides and formation of an intermediate palladium vinyl complex that could undergo subsequent Sonogashira reaction with a second alkyne molecule. This alkylation–alkynylation sequence allowed the one-step synthesis of 1,3-enynes including heteroarenes and biologically active compounds with high efficiency without exogenous photosensitizers or oxidants and now opens up pathways towards cascade reactions via photochemical palladium catalysis.

Manganese-Mediated Direct Functionalization of Hantzsch Esters with Alkyl Iodides via an Aromatization-Dearomatization Strategy

We report, for the first time, manganese-mediated direct functionalization of the Hantzsch esters with readily accessible alkyl iodides through an aromatization-dearomatization strategy. Applying this protocol, a library of valuable 4-alkyl-1,4-dihydropyridines were facilely afforded in good yields. This simple and practical reaction proceeds under visible-light irradiation at room temperature and displays high functional-group compatibility. Additionally, the method is applicable for gram-scale synthesis and late-stage functionalization of complex molecules.

Visible-light-mediated multicomponent reaction for secondary amine synthesis

The widespread presence of secondary amines in agrochemicals, pharmaceuticals, natural products, and small-molecule biological probes has inspired efforts to streamline the synthesis of molecules with this functional group. Herein, we report an operationally simple, mild protocol for the synthesis of secondary amines by three-component alkylation reactions of imines (generated in situ by condensation of benzaldehydes and anilines) with unactivated alkyl iodides catalyzed by inexpensive and readily available Mn2(CO)10. This protocol, which is compatible with a wide array of sensitive functional groups and does not require a large excess of the alkylating reagent, is a versatile, flexible tool for the synthesis of secondary amines.

Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator

Herein, we report a protocol for direct visible-light-mediated C-I difluoroallylation reactions of α-trifluoromethyl arylalkenes with alkyl iodides at room temperature with an α-aminoalkyl radical as a mediator. The protocol permits efficient functionalization of various α-trifluoromethyl arylalkenes with cyclic and acyclic primary, secondary, and tertiary alkyl iodides and is scalable to the gram level. This mild protocol uses an inexpensive mediator and is suitable for late-stage functionalization of complex natural products and drugs.

Scalable and Phosphine-Free Conversion of Alcohols to Carbon-Heteroatom Bonds through the Blue Light-Promoted Iodination Reaction

One of the fundamental and highly valuable transformations in organic chemistry is the nucleophilic substitution of alcohols. Traditionally, these reactions require strategies that employ stoichiometric hazardous reagents and are associated with difficulty in purification of the by-products. To overcome these challenges, here, we report a simple route toward the diverse conversion of alcohols via an SN2 pathway, in which blue light-promoted iodination is used to form alkyl iodide intermediates from simple unreactive alcohols. The scope of the process tolerates a range of nucleophiles to construct C-N, C-O, C-S, and C-C bonds. Furthermore, we also demonstrate that this method can be used for the preparation and late-stage functionalization of pharmaceuticals, as highlighted by the syntheses of thiocarlide, butoxycaine, and pramoxine.

A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies

N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.

Metal-Free Transfer Hydroiodination of C-C Multiple Bonds

The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.