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Preferential outcome of a chemical reaction
Chemoselectivity is the preferential reaction of a chemical reagent with one of two or more different functional groups. In a chemoselective system, a
Chemoselectivity
Chemical reagent
pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity, tolerance of sensitive functional groups, and a long shelf life. However
Dess–Martin_periodinane
Reduction of ketones and aldehydes to their corresponding alcohols
sacrificial alcohol. The advantages of the MPV reduction lie in its high chemoselectivity and its use of a cheap environmentally friendly metal catalyst. MPV
Meerwein–Ponndorf–Verley reduction
Meerwein–Ponndorf–Verley_reduction
Cross coupling reaction in organic chemistry
couple with chlorinated arenes. This low reactivity is the basis for chemoselectivity for nickel insertion into the C–Br bond of bromochlorobenzene using
Kumada_coupling
Chemical reaction
wide range of different types of ketones in both a stereoselective and chemoselective manner. Substrates include a large variety of aryl-aliphatic, di-aliphatic
Corey–Itsuno_reduction
tolerated. In this sense, chemoselectivity is sometimes referred to as functional group tolerance. Furthermore, high chemoselectivity avoids often undesired
Late-stage_functionalization
Large biological molecule that acts as a catalyst
therefore distinguish between very similar substrate molecules to be chemoselective, regioselective and stereospecific. Some of the enzymes showing the
Enzyme
Planned series of chemical reactions to produce desired product(s)
up chemical reactions with high specificity under mild conditions. Chemoselectivity ensures that a specific functional group in a molecule reacts while
Chemical_synthesis
Catalyst enabling the hydrogenation of alkynes to alkenes
of alkynes to alkenes without further reduction into alkanes (i.e. chemoselective semihydrogenation). It consists of palladium deposited on calcium carbonate
Lindlar_catalyst
addition across unactivated alkenes. Such transformations offer high chemoselectivity under mild conditions and have been increasingly applied in complex
Metal-hydride hydrogen atom transfer
Metal-hydride_hydrogen_atom_transfer
Organometallic coupling reaction
variations of the Grignard reagent have been discovered to improve the chemoselectivity of the Grignard reaction, which include but are not limited to: Turbo-Grignards
Grignard_reaction
display a higher degree of functional group tolerance and a much greater chemoselectivity. Generally, Hauser bases are used at room temperature while reactions
Hauser_base
Chemical compound
stoichiometric amount of sodium chlorite. TEMPO oxidations also exhibit chemoselectivity. In basic conditions, TEMPO oxidizes primary alcohols before secondary
TEMPO
Group of atoms introduced into a compound to prevent subsequent reactions
molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep
Protecting_group
Aqueous solution of hydrogen iodide
J. S. Dileep; Ho, ManKit M.; Toyokuni, Tatsushi (2001). "Simple and chemoselective reduction of aromatic nitro compounds to aromatic amines: reduction
Hydroiodic_acid
Chemical reaction
chemistry. As isocyanides exhibit high functional group tolerance, chemoselectivity, regioselectivity, and stereoselectivity, the Passerini reaction has
Passerini_reaction
Chemical reaction
cobalt complexes with Schiff base and porphyrin ligands. Due to its chemoselectivity (tolerant of other functional groups) and mild reactions conditions
Mukaiyama_hydration
Conversion of a carbonyl to an amine
considerations to be made when designing a reductive amination reaction. Chemoselectivity issues may arise since the carbonyl group can also be reduced. The
Reductive_amination
Chemical compound
powerful single-electron reducing agent, it does display remarkable chemoselectivity among functional groups. For example, sulfones and sulfoxides can be
Samarium(II)_iodide
Chemical ligation is the chemoselective condensation of unprotected peptide segments enabled by the formation of a non-native bond at the ligation site
Chemical_ligation
Organosulfur compounds of the form R–SC(=O)–R′
pub2. ISBN 978-3-527-30673-2. McGrath, N. A.; Raines, R. T. (2011). "Chemoselectivity in chemical biology: Acyl transfer reactions with sulfur and selenium"
Thioester
Measurement of infrared radiation's interaction with matter
Akula, Venugopal (2021-09-05). "Influence of Brønsted acid sites on chemoselective synthesis of pyrrolidones over H-ZSM-5 supported copper catalyst". Applied
Infrared_spectroscopy
Topics referred to by the same term
in biology Reactivity–selectivity principle, in general chemistry Chemoselectivity, a term used in organic chemistry to describe reactivity of one functional
Selectivity
Preference of chemical bonding or breaking in one direction over others
aromatic ring to give acetyl aromatic esters instead of methyl benzoates. Chemoselectivity Cryptoregiochemistry Enantioselectivity Keto–enol tautomerism Stereoselectivity
Regioselectivity
Chemical compound
5-nitro-3-trifluoromethylpyridine-2-carbonitrile [573762-57-9] (3). Chemoselective reduction of the nitro group involved a catalyst slurry (H3PO2, Pt/C
Apalutamide
Chemical compound
Since sodium cyanoborohydride is a mild reducing agent, it gives good chemoselectivity for reaction with certain functional groups in the presence of others
Sodium_cyanoborohydride
Chemical modification
molecule that can be removed with light. PPGs enable high degrees of chemoselectivity as they allow researchers to control spatial, temporal and concentration
Photolabile_protecting_group
Organic compounds of the form R–O–N=O
Nitrosation. Cambridge, UK: Cambridge University. p. 16. ISBN 0-521-26796-X. Chemoselective Nitration of Phenols with tert-Butyl Nitrite in Solution and on Solid
Alkyl_nitrite
American organic chemist
2008). "Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches". Nature. 456 (7221): 485–488. Bibcode:2008Natur.456..485T
Guangbin_Dong
Representation method in chemistry
molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction, facilitating multistep organic synthesis
Skeletal_formula
Organic compound containing an –NO2 group
2014.926373. S2CID 98439096. Shrinidhi, A. (2015). "Microwave-assisted chemoselective reduction of conjugated nitroalkenes to nitroalkanes with aqueous tri-n-butyltin
Nitro_compound
American chemist (born 1928)
aziridines. Two sulfur ylide variants have been employed that give different chemoselective products (scheme 21).The dimethylsulfoxonium methylide provides epoxides
Elias_James_Corey
Polyatomic ion
catalytic properties. Lanthanide-containing polyoxometalates show chemoselectivity and are also able to form inorganic–organic adducts, which can be exploited
Polyoxometalate
Primary alcohol
situ from NaBH4 and CeCl3(H2O)7. The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehydes or towards α,β-unsaturated
Luche_reduction
Study of compounds with carbon to zinc bonds
such as ketone, acetate, aromatic halides, and even aldehydes. The chemoselectivity observed indicates ketone formation is more facile than oxidative addition
Organozinc_chemistry
Chemical compound
Lebreton, Jacques (2025-07-16). "SDMA (Synhydrid, Red-Al, Vitride): A Chemoselective and Safe Solution for Reduction Reactions". Organic Process Research
Sodium bis(2-methoxyethoxy)aluminium hydride
Sodium_bis(2-methoxyethoxy)aluminium_hydride
Organic compound containing a –C(=O)OH group
N-Dimethyl(chloromethylene)ammonium chloride; [ClHC=N+(CH3)2]Cl−) is a highly chemoselective agent for carboxylic acid reduction. It selectively activates the carboxylic
Carboxylic_acid
Organic compound containing C–PO(OR)2 groups
ISBN 9780857090287. Carlson, Erin E.; Cravatt, Benjamin F. (2007). "Chemoselective probes for metabolite enrichment and profiling". Nature Methods. 4 (5):
Phosphonate
Experiment testing the origin of life
Pierre; Islam, Saidul; Powner, Matthew W. (2019). "Peptide ligation by chemoselective aminonitrile coupling in water". Nature. 571 (7766): 546–549. doi:10
Miller–Urey_experiment
Sulfonyl group organic reaction
and stereoselectivity. Aluminum amalgam (Al/Hg) may be used for the chemoselective reduction of α-sulfonylated carbonyl groups. Carboxylic acid derivatives
Reductive_desulfonylation
Nanoparticle technology
grown with particular functional groups on their surfaces that induce chemoselectivity. Functional biomolecules like transferrin, insulin, and folic acid
Protein_corona
Chemical reaction
cycle; see the Milas hydroxylation. Drawbacks of peroxides include chemoselectivity issues. Trialkylammonium N-oxides, such as NMO—as in the Upjohn Reaction—and
Sharpless asymmetric dihydroxylation
Sharpless_asymmetric_dihydroxylation
ineffective on the chosen substrates. Following this, a method for chemoselective methylenation of ketones in the presence of aldehydes and for aldehydes
Takai-Oshima-Lombardo methylenation
Takai-Oshima-Lombardo_methylenation
H-O bond. Regardless it is this step that kinetically imparts the chemoselectivity to the overall transformation. Stronger, more electron-rich bonds are
Shilov_system
Production of peptides
chemical ligation, in which unprotected peptide chains are condensed chemoselectively in aqueous solution by formation of a non-peptide bond. The most commonly
Peptide_synthesis
Thomson Reuters. Hoveyda's research focuses on the development for chemoselective and stereoselective catalysis, in particular function-oriented catalyst
Amir_H._Hoveyda
discovered and described in 2018. At low temperature, the reactions occur chemoselectively leading exclusively to adducts of pincer-[4+2] cycloaddition (5). The
Thermodynamic and kinetic reaction control
Thermodynamic_and_kinetic_reaction_control
Class of organic compounds
1002/(issn)1521-3773a. "Zirconium Tetrachloride (ZrCl4) Catalyzed Highly Chemoselective and Efficient Acetalization of Carbonyl Compounds". www.organic-chemistry
Diol
Chemical compound
saponification. Since BBP contains two ester bonds it is difficult to perform a chemoselective reaction. Under basic conditions BBP can undergo saponification. The
Benzyl_butyl_phthalate
Principle in chemical kinetics
(1996). "Organotin-Mediated Monoacylation of Diols with Reversed Chemoselectivity". Journal of Organic Chemistry. 61 (16): 5257–5263. doi:10.1021/jo960453f
Curtin–Hammett_principle
DNA oligonucleotides that can perform a specific chemical reaction
interest are DNA ligases. These molecules have demonstrated remarkable chemoselectivity in RNA branching reactions. Although each repeating unit in a RNA strand
Deoxyribozyme
Chemical compound
trimethylsulfoxonium iodide. Use of that reagent ensures the required chemoselectivity so that methylation occurs on the nitrogen atom of the pyrimidone.
Raltegravir
synthesis of N-aryl pyrrolidines from γ-(N-arylamino) alkenes: evidence for chemoselective alkene insertion into Pd–N bonds". Angew. Chem. Int. Ed. 43 (27): 3605–3608
Alkene_carboamination
Chemical compound
10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds". Chemistry:
DOTA_(chelator)
Chemical compound
asymmetric Strecker amino acid synthesis at the (2S)-α carbon. Secondly, chemoselective inner ring closure by fluorocyclization between 6-hydroxytrytophan and
Α-Amanitin
Amido magnesium halides containing significant lithium chloride components
Turbo-Hauser bases display a high functional group tolerance and greater chemoselectivity at high and low temperatures. The resulting reagent is then quenched
Turbo-Hauser_bases
Protecting group used in organic synthesis
Chankeshwara, Sunay V.; Chakraborti, Asit K. (2006). "Catalyst-Free Chemoselective N-tert-Butyloxycarbonylation of Amines in Water". Org. Lett. 8 (15):
Tert-Butyloxycarbonyl protecting group
Tert-Butyloxycarbonyl_protecting_group
Ability of a chemical reaction to produce an unequal mixture of stereoisomers
(−)-pinoresinol. Dynamic stereochemistry Torquoselectivity Regioselectivity Chemoselectivity (a)"Overlap Control of Carbanionoid Reactions. I. Stereoselectivity
Stereoselectivity
requires efficient native peptide ligation methods, which enable the chemoselective formation of a native peptide bond in aqueous solution between unprotected
SEA_Native_Peptide_Ligation
Chemical reaction
Without the presence of a directing group on the olefin, very little chemoselectivity is observed. However, an alkene which is significantly more nucleophilic
Simmons–Smith_reaction
Coenzyme, notable for its synthesis and oxidation role
Dejan-Krešimir; Powner, Matthew W. (22 February 2024). "Prebiotically plausible chemoselective pantetheine synthesis in water". Science. 383 (6685): 911–918. Bibcode:2024Sci
Coenzyme_A
Chemical compound
hydrogenation. Casey, Charles P.; Guan, Hairong (2007). "An Efficient and Chemoselective Iron Catalyst for the Hydrogenation of Ketones". Journal of the American
Knölker_complex
Spanish chemist
isomerization, epoxidation, chemo selective oxidation of alcohols and chemoselective hydrogenations. Corma Canós was elected a member of the National Academy
Avel·lí_Corma_Canós
American organic chemist (born 1977)
Radical-mediated C-H functionalization (alcohols to 1,3-diols) (2008) Chemoselective N-tert-Prenylation of Indoles by C–H Functionalization (2009) C-H trifluoromethylation
Phil_S._Baran
Chemical reaction
(2016-07-06). "Total Synthesis of (+)-SCH 351448: Efficiency via Chemoselectivity and Redox-Economy Powered by Metal Catalysis". Journal of the American
Carbonyl_allylation
Chemical reaction
Carolyn R. (July 2000). "A "Traceless" Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds". Organic Letters. 2 (14): 2141–1943. doi:10
Staudinger_reaction
Chemical way to synthesize proteins
acyl shift) amide-forming step under the reaction conditions used. Chemoselectivity of NCL : No side-products are formed from reaction with the other functional
Native_chemical_ligation
Organic redox reaction in chemistry
secondary alcohols are oxidized much faster than primary alcohols, thus chemoselectivity can be achieved. Furthermore, there is no over oxidation of aldehydes
Oppenauer_oxidation
Chemical reaction
considerable importance in synthetic organic chemistry due to its high chemoselectivity, mild reaction conditions, and the use of less-toxic reagents. In particular
Fukuyama_coupling
Chemical process
and of the N- and C- terminus. However, these reactions often lack chemoselectivity and efficiency, because they depend on the presence of native amino
Bioconjugation
Chemical compound
Skobridis; Vassiliki Theodorou; Edwin Weber (2006). "A very simple and chemoselective air oxidation of benzoins to benzils using alumina". Arkivoc. 06-1798JP:
Benzoin_(organic_compound)
cross-coupling event. They discovered that the C–P bond formation shows high chemoselectivity with a variety of aryl halides and excellent stereocontrol in the formation
Phosphoramidite_ligand
Chemical compound
; Ingram, Andrew J.; Zare, Richard N.; Waymouth, Robert M. (2013). "Chemoselective Pd-Catalyzed Oxidation of Polyols: Synthetic Scope and Mechanistic Studies"
Dihydroxyacetone
Chemical compound
1016/S0040-4039(00)77257-1. ISSN 0040-4039. McGeary, Ross P. (1998). "Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium
BOP_reagent
Organic molecule containing a neutral carbon with two unbound valence electrons
ISBN 978-0471238966. Yang, Peng; Yang, Wantai (2013-07-10). "Surface Chemoselective Phototransformation of C–H Bonds on Organic Polymeric Materials and
Carbene
Scientific study of chemical processes involving metabolites
analysis of carbonyl metabolites in human urine and fecal samples using chemoselective modification". The Analyst. 145 (11): 3822–3831. Bibcode:2020Ana...145
Metabolomics
Topics referred to by the same term
linking of two ends of DNA or RNA molecules Chemical ligation, the chemoselective condensation of unprotected peptides In medicine, the making of a ligature
Ligation
Chemical reaction that joins diazonium (R–N≡N) to an aromatic compound
Sarah B.; Italia, James S.; Chatterjee, Abhishek (2017-08-30). "A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation"
Azo_coupling
Chemical reaction
imine. Intermolecular Rauhut–Currier reactions typically exhibit poor chemoselectivity, because the reaction couples two activated alkenes, but intramolecular
Baylis–Hillman_reaction
Chemical compound
racemate, are commercially available. One of the wide applications include chemoselective hydrogenation, where BINAP is conjugated to rhodium. Berthod, Mikaël;
BINAP
reactivity, the transformations of organogermanes can exhibit excellent chemoselectivity and tolerate other reactive functional groups, which can provide a
Organogermanium compounds in cross-coupling reactions
Organogermanium_compounds_in_cross-coupling_reactions
German chemist (born 1972)
Allenes and Vinylcyclopropanes: First Studies of Endo-Exo Selectivity, Chemoselectivity, Relative Stereochemistry, and Chirality Transfer. In: Journal of the
Frank_Glorius
Procedures for isolating and purifying products of a chemical reaction
Teskey, Christopher J.; Adler, Pauline; Maulide, Nuno (2017-11-15). "Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides". Journal of the
Work-up
Class of organosilicon compounds of the form R3Si–O–CR=CR2
reactions employ electron-deficient sulfonyl azides, which undergo chemoselective, uncatalyzed [3+2] cycloaddition to the silyl enol ether, followed by
Silyl_enol_ether
Pericyclic chemical reaction
from biological systems and therefore these functionalities can be chemoselectively reacted even in the cellular context. They also do not react with other
1,3-Dipolar_cycloaddition
Chemical reaction
organocopper reagents, which are very reactive and are known to have low chemoselectivity, enough to destroy functional groups on both coupling partners, organosilicon
Hiyama_coupling
Chemical reaction
(2005). "Addition of Tethered Nonaromatic Carbon Nucleophiles to Chemoselectively Activated Amides". Org. Lett. 7 (20): 4431–4. doi:10.1021/ol0516519
Vilsmeier–Haack_reaction
Chemical compound
582J. doi:10.1002/zaac.200400464. Shimizu, M.; Hachiya, I. (2014). "Chemoselective Reductions and Iodinations using Titanium Tetraiodide". Tetrahedron
Titanium_tetraiodide
Chemical reaction
2024). "Applying a Guided Inquiry Approach to a Classic Practical on Chemoselective Reduction". Journal of Chemical Education. 101 (8): 3434–3444. doi:10
Reduction_of_nitro_compounds
1021/cr100207h. PMID 21033737. R. A. Miller; R. S. Hoerrner (2003). "Iodine as a Chemoselective Reoxidant of TEMPO: Application to the Oxidation of Alcohols to Aldehydes
Reoxidant
Chemical compound
Amin; Akradi, Jamal (2010). "A highly efficient, green, rapid, and chemoselective oxidation of sulfides using hydrogen peroxide and boric acid as the
Diethyl_sulfoxide
rearrangement. Bode, Jeffrey W.; Fox, Ryan M.; Baucom, Kyle D. (2006). "Chemoselective Amide Ligations by Decarboxylative Condensations ofN-Alkylhydroxylamines
KAHA_Ligation
Chemical compound
201310788. Casey, Charles P.; Guan, Hairong (2007). "An Efficient and Chemoselective Iron Catalyst for the Hydrogenation of Ketones". Journal of the American
Cyclopentadienone
Chemical compound
similar reactions. Iron(III) fluoride has also been shown to catalyze chemoselective addition of cyanide to aldehydes to give the cyanohydrins. The anhydrous
Iron(III)_fluoride
lower synthesis costs. Peptides are ideally covalently linked through a chemoselective bond leading to peptides with the same orientation for interaction profiling
Peptide_microarray
Chemical compound
Gaviño, Rubén (May–June 2005). "A mild and efficient method for the chemoselective synthesis of acylals from aromatic aldehydes and their deprotections
Acylal
Chemical compound
"Mixed solvents containing methanol as useful reaction media for unique chemoselective reductions within lithium borohydride". The Journal of Organic Chemistry
Lithium_borohydride
Pure chemical substances produced by and for the chemical industry
particularly with regard to stereoselectivity, regioselectivity, and chemoselectivity. They can also be modified ("reshuffled") for specific reactions, for
Fine_chemical
Pharmaceutical drug
The leurosine pathway uses the Nugent–RajanBabu reagent in a highly chemoselective de-oxygenation of leurosine. Anhydrovinblastine is then reacted sequentially
Vinorelbine
German chemist
formations based on an enamine mechanism. High reactivity, stereo- and chemoselectivity for aldol or conjugate addition reactions can be achieved by varying
Helma_Wennemers
travel, tourism, insurance
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
CHEMOSELECTIVITY
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